Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis : Novel ...

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X R 1 434 R 2 R 1 432 X + A NO 2 R 2 N(OSiMe 3) 2 R 2 X− N(OSiMe3) 2 R 1 SILYLATION OF NITRO COMPOUNDS AS A PROCESS 671 Me 3SiX X2; 2 Bu4NOAc CH2Cl2, −78 ο to 0 ο C R 2 O X R1 437 N OSiMe 3 AcO − Me 3SiX R 2 Me 3SiX NO 2 R 1 436 62%–95% AcOSiMe 3 + X − X 2 - Br 2 or I 2; R 1 = MeOCO(CH 2) 2, Bn, CH 2OSiMe 2Bu t , Me, Ph, H; R 2 = H, Me, n-C 5H 11. R 2 R 1 O N SiX/Base R 2 O O N R 1 Scheme 3.234 Ar Ar Ar 438 E X E + X − SiOTf E + OTf + SiX 430 OSi Scheme 3.235 E + X − Bu4N + AcO − R 2 R 1 R 2 R 1 A O N + Ar O N 439 OSi X − O E X − or AcO − SiX or AcOSi E
672 NITRONATES Table 3.30 The approach to functionalization of substituent at C-3 atom of six-membered cyclic nitronates (see Scheme 3.235) Yield of 439 Entry Ar R 1 R 2 Si X E 439 %% dr 1 Ph Me Me SiMe3OTf PhCH(OMe) a 71 1.8:1 2 Ph Me Me SiMe3OTf p-ClC6H4- CH(OMe) b 46 1.3:1 3 Ph Me Me SiMe3OTf p-MeOC6H4- CH(OMe) c 68 1:1 4 Ph Me Me SiMe3 Br a Br d 83 - 5 Ph Me Me SiMe3 I a I e 76 - 6 Ph MeO Me SiMe3 Cl 4MeC6H4S f 72 - 7 4-MeO- EtO H SiMe3 Cl 4ClC6H4S g 76 - C6H4 8 Ph H n-BuO SiMe2But 9 Ph n-BuO H SiMe2Bu OTf PhCH(OMe) h 45 2:1 t 10 Ph H n-BuO SiMe2Bu OTf PhCH(OMe) i 55 2.4:1 t OTf 4-MeO-C6H4 CH(OMe) j 55 2.7:1 11 Ph H n-BuO SiMe2But OTf CH2NMe2 k 89 - a With n-Bu4N + OAc − . sequences (515). The cations E + can be generated with the use of substrates E–X containing a good nucleofuge X − . The catalysis with Lewis acids can also be used. The approach shown in Scheme 3.235 and Table 3.30 makes it possible to functionalize the methyl group at C-3 in various six-membered cyclic nitronates. 3-Halomethyl-substituted nitronates (439 d,e) are particularly interesting reagents, which cannot be synthesized by known methods. It should be emphasized that the conÞgurations of the stereocenters at the endocyclic carbon atoms are retained in the transformation (438→439). Unfortunately, the diastereoselectivity of the generation of a new stereocenter in nitronates (439) is low; the resulting stereoisomers can be separated by chromatography. 3.5.4.2.2. Reactions of BENA with Nucleophiles The interaction of BENAs with nucleophiles at the β-C atom have been known since the discovery of BENA (188, 464), and these transformations were considered as SN2 ′ processes (Scheme 3.236). The existence of the stable conformation B of BENA (see Section 3.5.4.1. Fig. 3.3), in which the stabilizing πσ* interaction is favorable for elimination of the siloxy anion, supports this interpretation. However, more recent evidence contradicts the above described mechanism of the reaction of BENA with nucleophiles. The mechanistic aspect of the reactions of polyazoles and their N -silyl derivatives with BENA has been studied in most
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NITRILE OXIDES, NITRONES, AND NITRO
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NITRILE OXIDES, NITRONES, AND NITRO
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CONTENTS Series Foreword vii List o
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LIST OF ABBREVIATIONS AIBN 2,2’-a
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LIST OF ABBREVIATIONS xi RC radical
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2 NITRILE OXIDES + − − + + −
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4 NITRILE OXIDES NaOHa1 R-CH=NOH Na
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6 NITRILE OXIDES ammonium nitrate (
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8 NITRILE OXIDES R O N N R′ N NO
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10 NITRILE OXIDES HON C(NO 2) Me Me
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12 NITRILE OXIDES which rapidly eli
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14 NITRILE OXIDES Dimethyl furoxan-
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16 NITRILE OXIDES R2P(O)C=NOH N(CH2
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18 NITRILE OXIDES obtained by the s
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20 NITRILE OXIDES (136, 137), appli
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22 NITRILE OXIDES RCNO + R′CH=CH2
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24 NITRILE OXIDES aldehydes are bei
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26 NITRILE OXIDES R Cr(CO)3 Ar = 3,
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28 NITRILE OXIDES bonding effect. T
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30 NITRILE OXIDES Selective nitrile
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32 NITRILE OXIDES H H H RCNO + R =
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34 NITRILE OXIDES O O O Br ArCNO Ar
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36 NITRILE OXIDES the bridgehead po
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38 NITRILE OXIDES O O OR′ H H 94
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40 NITRILE OXIDES H O N H O O R 101
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42 NITRILE OXIDES O O 111 CH(OMe)2
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44 NITRILE OXIDES Ph2CHCO N H2C N M
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46 NITRILE OXIDES O (Me 2CHO) 2P N
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48 NITRILE OXIDES R 137a-f PhCNO N
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50 NITRILE OXIDES R N Ph N O O Ph R
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52 NITRILE OXIDES derivatives 4-R 2
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54 NITRILE OXIDES OH N H (CH2)n R N
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56 NITRILE OXIDES Ar R 1 N 174 N O
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58 NITRILE OXIDES N-benzyladamantyl
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60 NITRILE OXIDES Ph3P L Rh O 194 N
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62 NITRILE OXIDES and modern prepar
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64 NITRILE OXIDES R 2 = MeO2C, R 3
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66 NITRILE OXIDES 223 with 2-iodoni
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68 NITRILE OXIDES N O O N N N R R R
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70 NITRILE OXIDES complexes [PdCl2(
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72 NITRILE OXIDES measured for the
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74 NITRILE OXIDES Oxidation of (alk
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76 NITRILE OXIDES electrophiles as
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78 NITRILE OXIDES O 2N Ph R S N ONC
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80 NITRILE OXIDES PhCH 2Co(dmgH) 2p
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82 NITRILE OXIDES are formed exclus
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84 NITRILE OXIDES On treatment with
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86 NITRILE OXIDES PhSO 2 R R′C=NO
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88 NITRILE OXIDES R X = OTMS O O H
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90 NITRILE OXIDES TBSO H Me NOH TBS
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92 NITRILE OXIDES A synthetic appro
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94 NITRILE OXIDES N O H CO 2Me H 2N
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96 NITRILE OXIDES the unambiguous a
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98 NITRILE OXIDES t-Bu t-Bu O O O O
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100 NITRILE OXIDES COX-2 selectivit
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102 NITRILE OXIDES elastase release
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104 NITRILE OXIDES ambient temperat
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106 NITRILE OXIDES HO Ph O N O O N
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108 NITRILE OXIDES and acceptor sub
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110 NITRILE OXIDES 31. Belen’kii
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112 NITRILE OXIDES 87. Matt Ch, Gis
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114 NITRILE OXIDES 146. Faita G, Pa
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116 NITRILE OXIDES 208. Gravestock
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118 NITRILE OXIDES 266. Tian L, Xu
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120 NITRILE OXIDES 324. Stajer G, B
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122 NITRILE OXIDES 382. Himo F, Lov
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124 NITRILE OXIDES 445. Yamamoto T,
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126 NITRILE OXIDES 504. D’ Alelio
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2 Nitrones: Novel Strategies in Syn
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SYNTHESIS OF NITRONES 131 Treated w
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R H OH R N R Oxone K2CO3 OH R N O S
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H N H RO R N H N H CO2H OH O OR P O
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R1 − − R N O 1-CH2-NH-R2 2 BF4
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O N+ O − (EtO) 2P XCH2CN (X = Cl,
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Et H3CO H 3CO − O R R N 1 H N H O
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[O] SYNTHESIS OF NITRONES 143 N H N
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(R 1 O)m O 47 ( )n OH + RNHOH (R 1
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R 5 R 6 R 5 R 6 R6 R5 O R 1 R5 R R6
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+ N O − (EtO)2(O)P HO (EtO)2(O)P
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H O − N O 166, 167 AZN O N − +
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AcO OAc OAc O OAc O OAc OAc O OAc O
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SYNTHESIS OF NITRONES 155 Similarly
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O Ph Et 2N R R 1 S CHO N COOEt R =
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SYNTHESIS OF NITRONES 159 In a simi
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SYNTHESIS OF NITRONES 161 (EtO) 2(O
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R 2 R 1 Cl Ph O · Cl Ph N OR Ph N
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R 1 NO2 R 2 PhSeH R 1 (EtO)2(O)PCH2
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HO MeO2C Br "N-exo" O O O MeO2C 105
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R O N H Ar * SeOTF CH 2Cl 2 R O N H
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SYNTHESIS OF NITRONES 171 (where R
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2 PhCH = NONa H 150 N OH + R 1 R 2
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R 2 R 3 H R 1 R 1 R 2 N O + N OH 16
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R 1 R 2 − O + N OOH R 1 R 2 O OMe
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[R1R2C(NO2)] − + M R3 178 175 (R
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R R R R 188 189 NHOH a: R = Me b: R
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STRUCTURE AND SPECTRA OF NITRONES 1
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R R H C N O + H 3C Bu t + C STRUCTU
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I R 1 − O R 2 ( )n − ( )n N O
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Bu t Ph O N OH − + H H H CF 3 Ph
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Bu N t H O + + N N − − ROCCH2 O
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STRUCTURE AND SPECTRA OF NITRONES 1
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ELECTROCHEMICAL PROPERTIES AND EPR-
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R 2 R 1 N O ELECTROCHEMICAL PROPERT
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NITRONE COMPLEXES 203 radiolysis in
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R 2 226a-c R 1 N O + O N − + −
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R 2 R O C N 1 R2 R3 + R 1 , R 2 , R
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OH _ O + N R 1 a: R 1 = Me, b: R 1
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R Me Me Me Me H N H 259 O O 255a-c
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NITRONE REACTIONS 213 2.6.2. Reduct
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N + O − • + ClO 2 N O • H O C
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H O + N DMPO H O N N 228-232 MeOH P
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Ph H3CO H3CO Ph N O 276 N O 281 O
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Ph N O N F • Ph + Ph F Ph R F Ph
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Ph Ph O O + N O − 286 Rl,Et 3B be
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Table 2.9 Electroreductive coupling
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NITRONE REACTIONS 227 This reaction
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295a Br I NaOH, MeOH NaOH, MeOH NaO
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H 3C R H3C N O − + O N CH3 CH 3 C
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H + O N B− − − − H N − BH
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H H X + O N H RLi O N E X = CH2, NC
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NITRONE REACTIONS 237 Nucleophilic
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O BnO Ph Et 2N O BnO H 317 O O HO N
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NH 2 NH 2 Boc N H2N N(OH)Bn Boc N P
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NITRONE REACTIONS 243 EtAlCl2, TiCl
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NITRONE REACTIONS 245 Addition of v
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HO R R R HO N Bn NHBoc NH 2 NHBoc N
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RCHO BocNHOH R 2 + + O N R1 − PhS
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BzlOOC + NH3 Cl i OH BzlO Cl Cl Bzl
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Table 2.12 Addition a of 2-lithiofu
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H 2N O BnO O OH O CO2H H2N O N H OH
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353 b a BnO BnO 354 Bn N CHO OBn b
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Table 2.13 Addition of organolithiu
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R N O Cl 367 −O + N Bu t LDA, THF
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HO HO OH N N • Ph • O OH O HO P
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RO2C N O X • N O • N O N O •
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N O 373 N O a 374, 376, 377 R2 376
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+ N O − HN HO O R1 S R2 R3 + Ph 1
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+ R 1 N R2 O O R 1 N R 2 − R 1 R
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NITRONE REACTIONS 273 Table 2.14 Sy
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+ Ph N O − Bn + O Et 3SiO MeO O H
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O O O N Pri OCOPh R Me Bn CO 2H NHC
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N O OBu t N O THF,−78°C, 1 h OBu
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O O O O 292 O H N −O + Bn O HO N
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NITRONE REACTIONS 283 The reaction
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O − O O BnO O O + O − O − N P
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R 1 R 2 NH 2 COOH Br a: b: c: d: e:
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NITRONE REACTIONS 289 2.6.6.1.11. N
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NITRONE REACTIONS 291 Nucleophilic
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O − O O + NBoc− O NBoc N Bn 1.
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NITRONE APPLICATION IN RADICAL POLY
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REACTIONS OF DIPOLAR 1,3-CYCLOADDIT
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a b c d REACTIONS OF DIPOLAR 1,3-CY
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R REACTIONS OF DIPOLAR 1,3-CYCLOADD
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a REACTIONS OF DIPOLAR 1,3-CYCLOADD
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− REACTIONS OF DIPOLAR 1,3-CYCLOA
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(a) REACTIONS OF DIPOLAR 1,3-CYCLOA
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O HO REACTIONS OF DIPOLAR 1,3-CYCLO
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Bn REACTIONS OF DIPOLAR 1,3-CYCLOAD
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CO 2Me O O REACTIONS OF DIPOLAR 1,3
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H H REACTIONS OF DIPOLAR 1,3-CYCLOA
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Me REACTIONS OF DIPOLAR 1,3-CYCLOAD
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O REACTIONS OF DIPOLAR 1,3-CYCLOADD
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Ph Ph REACTIONS OF DIPOLAR 1,3-CYCL
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− O Me REACTIONS OF DIPOLAR 1,3-C
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Ph REACTIONS OF DIPOLAR 1,3-CYCLOAD
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B C A Closed [5,6] adduct B B KINUG
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KINUGASA REACTION ([2 + 2] CYCLOADD
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O O N N N O R R O O L 1 : N N N 1 m
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R 1 R 1 O + N 774 a-e Δ O N N Ph 1
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783 784 + N O + CH3 − N O Ph CH3
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R 1 NHOH 793 + R 2 CHO 794 Hydroxyl
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REACTIONS WITH CYCLOPROPANES 397 O
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REFERENCES 399 properties and synth
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REFERENCES 401 (d) Mottley C, Mason
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REFERENCES 403 46. Sankuratri N, Ja
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REFERENCES 405 105. Saladino R, Ner
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REFERENCES 407 159. Sridharan V, Mu
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REFERENCES 409 205. Cupone G, De Ni
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REFERENCES 411 259. Balasundaram B,
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REFERENCES 413 310. (a) Cicchi S, M
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REFERENCES 415 (b) Creary X. Acc. C
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REFERENCES 417 410. Dziembowska T,
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REFERENCES 419 459. Bourquet E, Ban
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REFERENCES 421 Papers of 6-th Inter
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REFERENCES 423 573. Ok D, Fisher MH
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REFERENCES 425 636. (a) Jost S, Gim
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REFERENCES 427 690. Haire DL, Janze
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REFERENCES 429 721. Manzoni L, Aros
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REFERENCES 431 762. Baldwin JE, Adl
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REFERENCES 433 808. Leggio A, Liguo
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3 Nitronates SEMA L. IOFFE N. D. Ze
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SYNTHESIS OF NITRONATES 437 as O-nu
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SYNTHESIS OF NITRONATES 439 These r
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SYNTHESIS OF NITRONATES 441 It shou
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X-C(NO 2) 3 NO 2-C(NO 2) 3 R R′ C
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R R′ X NO 2 base −H + R R′ X
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Br NaNO 2/DMF Cl R 6 R=C6H5; CO2MeR
Page 464 and 465:
OH NO 2 R EtO2CN NCO 2Et PPh 3, ben
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NO 2 O Me R 2 R 1 PhSH Et 3N cat. M
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R R O OAc 19 Mn III −H + NO2 Me M
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Ag[ArC(NO2)2] 26 heptane 100°, 50
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NO2CH=C(NO2)Ph [RR′CN 2 28 RR′C
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Me O 2N Me O 2N 29a Br EtO 2CC CCO
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SYNTHESIS OF NITRONATES 461 (39) (s
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SYNTHESIS OF NITRONATES 463 In the
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R 1 R R 2 NO 2 + R 5 R 3 42 43 R 6
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O O N R + R"CO NO2 R′ N 42 43c Ph
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SYNTHESIS OF NITRONATES 469 3.2.2.3
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R R′ C R H C R′ NO2 [RR′C(NO2
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Table 3.1 The silylation of AN by E
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SYNTHESIS OF NITRONATES 475 Table 3
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O Me 2RSi NMe 2 + − Me2N=C—OSiM
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SYNTHESIS OF NITRONATES 479 decompo
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A G N R O N H O O A Si R 1 RR 1 C=N
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NO2CH2CH2CH2CO2ME Me CO2Me NO2CH CH
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SYNTHESIS OF NITRONATES 485 than 20
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R 1 R 2 LDA THF, −78°C R 1 O OLi
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O R 1 N 51o-t OSiMe2R 3 R 2 PRINCIP
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MeO2C H PRINCIPAL PHYSICOCHEMICAL D
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PRINCIPAL PHYSICOCHEMICAL DATA AND
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R' R PRINCIPAL PHYSICOCHEMICAL DATA
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Table 3.8 (continued) PRINCIPAL PHY
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** NO2 O O N O * N SiMe3 O PRINCIPA
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XO R 1 N O H XO O N R R 2 = H R 3 X
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EtO 2CCH N(O)OMe Δ or HCl NH3 / Me
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R 1 R 2 OSi N O E—Nu R 1 R 2 REAC
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O OM R′ N 113 R′′ Me 3SiX −
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O O R 1 R 1 N N OSi R 2 OSi R 2 + M
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R 1 PhO2S R 1 PhO 2S N NO2 O OSiMe
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R 3 R 1 O R 4 R 3 R 3 R 1 R 1 55%-7
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RR′C N MeOCO MeO C O OBEt 2 N O O
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REACTIVITY OF NITRONATES 533 Yields
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RO R 4 R 3 R 2 O N R 1 O P(OAlk) 3
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REACTIVITY OF NITRONATES 537 Second
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MeO2C Ph CO2Me O N O X 1 X 2 Ph H R
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R CO2Me TiCl 4 reflux, overnight N
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Me NO2 + Ph Me NO 2 Ph + Bu n O Bu
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R R O2N O2N O N Regioselectivity +
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REACTIVITY OF NITRONATES 547 Ref.33
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REACTIVITY OF NITRONATES 549 Ref.52
Page 566 and 567:
MeO2C MeO 2C 160 N O OMe R OMgBr r.
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R N O N O R N O N O Y Z X xylene, r
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REACTIVITY OF NITRONATES 555 O N O
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RCH2NO2 RHC N RHC N O OH Ac 2O/AcON
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PhCOCH2SCHR′R′′ 180 R′R′
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REACTIVITY OF NITRONATES 561 Both o
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R 185 + R′ 195 NO2 OH ( )n KH; TH
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NaNO2 AcOH 199 200 (+) -citronellen
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O X X X X S 208 D F E SiMe3 NO 2 O
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R′ R′′ HO R O N 213 O ClSi R
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R SiO R AlkO N N R′′ O + R′
Page 588 and 589:
R′ R′ R′ R′ O N OSi 229 OH
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R′′ OH Si - Me2Bu t Si R′ R N
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R = Me R′ = Ph(86%);CO2Me(28%) O
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R′O HO OR′ R′′ R′ O N * *
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REACTIVITY OF NITRONATES 581 orient
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REACTIVITY OF NITRONATES 583 isomer
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O N O 249a-g + R′ 250a,b R O N O
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REACTIVITY OF NITRONATES 587 Experi
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BuO R 1 Me Me Me Et Et Et Me * ** O
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REACTIVITY OF NITRONATES 591 3.4.4.
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N N OH HO H H H HO (−)-hastinecin
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REACTIVITY OF NITRONATES 595 compli
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Four component [4+2] [4+2] [4+2] do
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Bn O O REACTIVITY OF NITRONATES 599
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Me2Si R 1 NO2 R 1 R 2 R 2 291 O EtO
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O 2N R * = EtO + 296 OEt R * OAc Et
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G * OH G * O G * OH: 305 306 OH Ph
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SILYLATION OF NITRO COMPOUNDS AS A
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RCH2CH2CHNO2 319 H a B − BH + SIL
Page 626 and 627:
R 1 R 2 Ph R2 R1 O N OSi NO2 R2 R1
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Page 630 and 631:
Me 2N CH 2 N OSiMe 3 R 1 R 2 + O N
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Ref.459 Ar Ar HF 2 − HF 2 − + N
Page 634 and 635:
R 2 R 3 R 1 NO 2 SiX/Et3N (1) SILYL
Page 636 and 637: NO 2 NO2 SiX/Et 3N NO 2 Me 3SiCl/DB
Page 638 and 639: SILYLATION OF NITRO COMPOUNDS AS A
Page 642 and 643: C N OH OH C N OH + + OH B Si - trio
Page 644 and 645: R 2 R3 R4 R 1 O N TfOH O 348f-h R 2
Page 648 and 649: R O N OX SILYLATION OF NITRO COMPOU
Page 652 and 653: Pheq O N O 356a TfOTBS Pheq O N 357
Page 654 and 655: (a) SiO O N 6 Nu (b) N N (c) SiO Si
Page 662 and 663: # N CO2Me OSi OMe SiO N CO2Me OSi S
Page 666 and 667: ( ) 3 H Ph O N OMe 391a H N Ph O N
Page 668 and 669: R 2 R 3 R 4 R 2 R 3 R 4 R 2 An O N
Page 670 and 671: R = CO2Me; NO2;Δ t > 50°C (O 2N)2
Page 672 and 673: X NO 2 SILYLATION OF NITRO COMPOUND
Page 682 and 683: O N An 431(C) OTMS SILYLATION OF NI
Page 684 and 685: R 1 432 R 1 434 E OR 3 NO2 R 2 N(OS
Page 688 and 689: Si - trialkylsilyl N OSi O Si SILYL
Page 690 and 691: R 1 R 2 441 R 1 R 2 NO2 C NO 2 −
Page 694 and 695: R 2 SILYLATION OF NITRO COMPOUNDS A
Page 698 and 699: NH 3 N H * + H 2C CO 2Et R 1 = H or
Page 700 and 701: N N N N R 1 =Me, R 2 =H 92% Bz Me N
Page 704 and 705: RN(NO2)SiMe3 RN N + 473a,b OSiMe3 i
Page 708 and 709: Cl N OSiMe3 MeO OSiMe3 Me 476d SILY
Page 710 and 711: R R 495 NO2 493 N(OTBS)2 R′I (Me3
Page 712 and 713: R 1 N(OSi)2 Nu: (b) R 2 EX (a) Si =
Page 716 and 717: Me Me Me Me Me Me Ph eq O 507a Ph N
Page 720 and 721: R 3 R 4 R 5 R 3 R 4 R 5 Et3N R 3 R
Page 722 and 723: R3 R2 R 4 NO2 O R 1 R 1 O N 521 R 2
Page 724 and 725: X R 2 R 1 NO2 ii For 528a iii For 5
Page 726 and 727: MeO2C MeO2C MeO2C 528a BSA 530a O N
Page 736 and 737:
Me 3SiO Me3SiO N Me3SiON Me 3Si H N
Page 738 and 739:
Page 740 and 741:
CONCLUSION 725 those containing fun
Page 742 and 743:
REFERENCES 727 Due to the silylatio
Page 744 and 745:
REFERENCES 729 35. Tartakovsky VA,
Page 746 and 747:
Page 748 and 749:
REFERENCES 733 158. University of I
Page 750 and 751:
REFERENCES 735 221. Kornilov VI, Pa
Page 752 and 753:
REFERENCES 737 273. Shitkin VM, Iof
Page 754 and 755:
REFERENCES 739 329. Harada K, Shimo
Page 756 and 757:
Page 758 and 759:
REFERENCES 743 437. Kim BH, Curran
Page 760 and 761:
REFERENCES 745 491. Ioffe SL, Lyapk
Page 762:
REFERENCES 747 540. Gilchrist TL, R
Page 765 and 766:
750 INDEX 1,3-Dipolar cycloaddition
Page 767 and 768:
752 INDEX Nitrone reactions (contd.
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Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis : Novel ...

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