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

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2 Nitrones: Novel Strategies in Synthesis IGOR ALEXEEVICH GRIGOR’EV Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences, Novosibirsk, Russia 2.1. INTRODUCTION For the last 50 years many scientists have drawn special attention to nitrones due to their successful application as building blocks in the synthesis of various natural and biologically active compounds, of stable nitroxyl radicals, and of other important products for special purposes such as spin traps for the study of radical processes including those that take place in biological systems, and they also found use as both, modiÞers and regulators of molecular weight in radical polymerization. Nowadays, a great deal of literature (1–4) is devoted to certain aspects of nitrone chemistry and its application, or to speciÞc classes of nitrones (5). However, at the present time, the reviews dealing with all or practically all aspects of nitrone chemistry, except those which are well-known and widely covered in the literature (6), are still lacking. The main aim of this work is to make an attempt to analyze all the aspects of nitrone chemistry and its application which have been developed over the last 15 years. The early works will also be considered to make comparisons, or if these works were not covered in previous reviews; but if, as we see it, without mentioning these works, the representation of the diverse chemistry of nitrones seems incomplete. To illustrate the multifaceted chemistry of nitrones and their application in synthesis, let us consider the synthetic scheme of bicyclic and tricyclic chiral ligands (Scheme 2.1) (7) as well as diastereo- and enantiostereoselective syntheses of alkaloids (Scheme 2.2) (8). Many successful chemical transformations based on the rich and multifaceted chemistry of nitrones underlie various synthetic strategies. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis: Novel Strategies in Synthesis, Second Edition, By Henry Feuer Copyright © 2008 John Wiley & Sons, Inc. 129
130 NITRONES: NOVEL STRATEGIES IN SYNTHESIS R 2 R 4 R 1 R 3 HO NH 2 R 2 R 4 R 1 R 3 HO N O Ph R 2 R 4 R 1 R 3 HO S O O R2 N O N O n * * N R 3 1. PhCHO 2. NaBH4 OR R 1 n R 5 HCl R 2 R 4 R 1 R 3 HO NH R 2 R 4 R 1 R 3 O R 6 R1 OR CH 2Ph HO NHOH.HCl R 7 2.2. SYNTHESIS OF NITRONES 2.2.1. Oxidative Methods Scheme 2.1 1. NaN(TMS)2 2. Cl 3. H3O+ NO Scheme 2.2 HO H 2O 2/Na 2WO 4 O R 7 R 5 O R 6 R 2 R 4 R 1 R 3 N H N O O R 6 H S O O O N H S O O O 2.2.1.1. Oxidation of Imines Oxidation of imines with peracids leads to oxaziridines, with the possibility of their successive rearrangement into nitrones, depending on their structure and the employed oxidant. R 7 O NH OH N O n n + − R 5 R1 R1
Page 2:
NITRILE OXIDES, NITRONES, AND NITRO
Page 6 and 7:
NITRILE OXIDES, NITRONES, AND NITRO
Page 8:
CONTENTS Series Foreword vii List o
Page 12 and 13:
LIST OF ABBREVIATIONS AIBN 2,2’-a
Page 14:
LIST OF ABBREVIATIONS xi RC radical
Page 17 and 18:
2 NITRILE OXIDES + − − + + −
Page 19 and 20:
4 NITRILE OXIDES NaOHa1 R-CH=NOH Na
Page 21 and 22:
6 NITRILE OXIDES ammonium nitrate (
Page 23 and 24:
8 NITRILE OXIDES R O N N R′ N NO
Page 25 and 26:
10 NITRILE OXIDES HON C(NO 2) Me Me
Page 27 and 28:
12 NITRILE OXIDES which rapidly eli
Page 29 and 30:
14 NITRILE OXIDES Dimethyl furoxan-
Page 31 and 32:
16 NITRILE OXIDES R2P(O)C=NOH N(CH2
Page 33 and 34:
18 NITRILE OXIDES obtained by the s
Page 35 and 36:
20 NITRILE OXIDES (136, 137), appli
Page 37 and 38:
22 NITRILE OXIDES RCNO + R′CH=CH2
Page 39 and 40:
24 NITRILE OXIDES aldehydes are bei
Page 41 and 42:
26 NITRILE OXIDES R Cr(CO)3 Ar = 3,
Page 43 and 44:
28 NITRILE OXIDES bonding effect. T
Page 45 and 46:
30 NITRILE OXIDES Selective nitrile
Page 47 and 48:
32 NITRILE OXIDES H H H RCNO + R =
Page 49 and 50:
34 NITRILE OXIDES O O O Br ArCNO Ar
Page 51 and 52:
36 NITRILE OXIDES the bridgehead po
Page 53 and 54:
38 NITRILE OXIDES O O OR′ H H 94
Page 55 and 56:
40 NITRILE OXIDES H O N H O O R 101
Page 57 and 58:
42 NITRILE OXIDES O O 111 CH(OMe)2
Page 59 and 60:
44 NITRILE OXIDES Ph2CHCO N H2C N M
Page 61 and 62:
46 NITRILE OXIDES O (Me 2CHO) 2P N
Page 63 and 64:
48 NITRILE OXIDES R 137a-f PhCNO N
Page 65 and 66:
50 NITRILE OXIDES R N Ph N O O Ph R
Page 67 and 68:
52 NITRILE OXIDES derivatives 4-R 2
Page 69 and 70:
54 NITRILE OXIDES OH N H (CH2)n R N
Page 71 and 72:
56 NITRILE OXIDES Ar R 1 N 174 N O
Page 73 and 74:
58 NITRILE OXIDES N-benzyladamantyl
Page 75 and 76:
60 NITRILE OXIDES Ph3P L Rh O 194 N
Page 77 and 78:
62 NITRILE OXIDES and modern prepar
Page 79 and 80:
64 NITRILE OXIDES R 2 = MeO2C, R 3
Page 81 and 82:
66 NITRILE OXIDES 223 with 2-iodoni
Page 83 and 84:
68 NITRILE OXIDES N O O N N N R R R
Page 85 and 86:
70 NITRILE OXIDES complexes [PdCl2(
Page 87 and 88:
72 NITRILE OXIDES measured for the
Page 89 and 90:
74 NITRILE OXIDES Oxidation of (alk
Page 91 and 92:
76 NITRILE OXIDES electrophiles as
Page 93 and 94: 78 NITRILE OXIDES O 2N Ph R S N ONC
Page 95 and 96: 80 NITRILE OXIDES PhCH 2Co(dmgH) 2p
Page 97 and 98: 82 NITRILE OXIDES are formed exclus
Page 99 and 100: 84 NITRILE OXIDES On treatment with
Page 101 and 102: 86 NITRILE OXIDES PhSO 2 R R′C=NO
Page 103 and 104: 88 NITRILE OXIDES R X = OTMS O O H
Page 105 and 106: 90 NITRILE OXIDES TBSO H Me NOH TBS
Page 107 and 108: 92 NITRILE OXIDES A synthetic appro
Page 109 and 110: 94 NITRILE OXIDES N O H CO 2Me H 2N
Page 111 and 112: 96 NITRILE OXIDES the unambiguous a
Page 113 and 114: 98 NITRILE OXIDES t-Bu t-Bu O O O O
Page 115 and 116: 100 NITRILE OXIDES COX-2 selectivit
Page 117 and 118: 102 NITRILE OXIDES elastase release
Page 119 and 120: 104 NITRILE OXIDES ambient temperat
Page 121 and 122: 106 NITRILE OXIDES HO Ph O N O O N
Page 123 and 124: 108 NITRILE OXIDES and acceptor sub
Page 125 and 126: 110 NITRILE OXIDES 31. Belen’kii
Page 127 and 128: 112 NITRILE OXIDES 87. Matt Ch, Gis
Page 129 and 130: 114 NITRILE OXIDES 146. Faita G, Pa
Page 131 and 132: 116 NITRILE OXIDES 208. Gravestock
Page 133 and 134: 118 NITRILE OXIDES 266. Tian L, Xu
Page 135 and 136: 120 NITRILE OXIDES 324. Stajer G, B
Page 137 and 138: 122 NITRILE OXIDES 382. Himo F, Lov
Page 139 and 140: 124 NITRILE OXIDES 445. Yamamoto T,
Page 141 and 142: 126 NITRILE OXIDES 504. D’ Alelio
Page 146 and 147: SYNTHESIS OF NITRONES 131 Treated w
Page 148 and 149: R H OH R N R Oxone K2CO3 OH R N O S
Page 150 and 151: H N H RO R N H N H CO2H OH O OR P O
Page 152 and 153: R1 − − R N O 1-CH2-NH-R2 2 BF4
Page 154 and 155: O N+ O − (EtO) 2P XCH2CN (X = Cl,
Page 156 and 157: Et H3CO H 3CO − O R R N 1 H N H O
Page 158 and 159: [O] SYNTHESIS OF NITRONES 143 N H N
Page 160 and 161: (R 1 O)m O 47 ( )n OH + RNHOH (R 1
Page 162 and 163: R 5 R 6 R 5 R 6 R6 R5 O R 1 R5 R R6
Page 164 and 165: + N O − (EtO)2(O)P HO (EtO)2(O)P
Page 166 and 167: H O − N O 166, 167 AZN O N − +
Page 168 and 169: AcO OAc OAc O OAc O OAc OAc O OAc O
Page 170 and 171: SYNTHESIS OF NITRONES 155 Similarly
Page 172 and 173: O Ph Et 2N R R 1 S CHO N COOEt R =
Page 174 and 175: SYNTHESIS OF NITRONES 159 In a simi
Page 176 and 177: SYNTHESIS OF NITRONES 161 (EtO) 2(O
Page 178 and 179: R 2 R 1 Cl Ph O · Cl Ph N OR Ph N
Page 180 and 181: R 1 NO2 R 2 PhSeH R 1 (EtO)2(O)PCH2
Page 182 and 183: HO MeO2C Br "N-exo" O O O MeO2C 105
Page 184 and 185: R O N H Ar * SeOTF CH 2Cl 2 R O N H
Page 186 and 187: SYNTHESIS OF NITRONES 171 (where R
Page 188 and 189: 2 PhCH = NONa H 150 N OH + R 1 R 2
Page 190 and 191: R 2 R 3 H R 1 R 1 R 2 N O + N OH 16
Page 192 and 193: R 1 R 2 − O + N OOH R 1 R 2 O OMe
Page 194 and 195:
[R1R2C(NO2)] − + M R3 178 175 (R
Page 196 and 197:
R R R R 188 189 NHOH a: R = Me b: R
Page 198 and 199:
STRUCTURE AND SPECTRA OF NITRONES 1
Page 200 and 201:
R R H C N O + H 3C Bu t + C STRUCTU
Page 202 and 203:
I R 1 − O R 2 ( )n − ( )n N O
Page 204 and 205:
Bu t Ph O N OH − + H H H CF 3 Ph
Page 206 and 207:
Bu N t H O + + N N − − ROCCH2 O
Page 208 and 209:
STRUCTURE AND SPECTRA OF NITRONES 1
Page 210 and 211:
ELECTROCHEMICAL PROPERTIES AND EPR-
Page 212 and 213:
Page 214 and 215:
R 2 R 1 N O ELECTROCHEMICAL PROPERT
Page 216 and 217:
Page 218 and 219:
NITRONE COMPLEXES 203 radiolysis in
Page 220 and 221:
R 2 226a-c R 1 N O + O N − + −
Page 222 and 223:
R 2 R O C N 1 R2 R3 + R 1 , R 2 , R
Page 224 and 225:
OH _ O + N R 1 a: R 1 = Me, b: R 1
Page 226 and 227:
R Me Me Me Me H N H 259 O O 255a-c
Page 228 and 229:
NITRONE REACTIONS 213 2.6.2. Reduct
Page 230 and 231:
N + O − • + ClO 2 N O • H O C
Page 232 and 233:
H O + N DMPO H O N N 228-232 MeOH P
Page 234 and 235:
Ph H3CO H3CO Ph N O 276 N O 281 O
Page 236 and 237:
Ph N O N F • Ph + Ph F Ph R F Ph
Page 238 and 239:
Ph Ph O O + N O − 286 Rl,Et 3B be
Page 240 and 241:
Table 2.9 Electroreductive coupling
Page 242 and 243:
NITRONE REACTIONS 227 This reaction
Page 244 and 245:
295a Br I NaOH, MeOH NaOH, MeOH NaO
Page 246 and 247:
H 3C R H3C N O − + O N CH3 CH 3 C
Page 248 and 249:
H + O N B− − − − H N − BH
Page 250 and 251:
H H X + O N H RLi O N E X = CH2, NC
Page 252 and 253:
NITRONE REACTIONS 237 Nucleophilic
Page 254 and 255:
O BnO Ph Et 2N O BnO H 317 O O HO N
Page 256 and 257:
NH 2 NH 2 Boc N H2N N(OH)Bn Boc N P
Page 258 and 259:
NITRONE REACTIONS 243 EtAlCl2, TiCl
Page 260 and 261:
NITRONE REACTIONS 245 Addition of v
Page 262 and 263:
HO R R R HO N Bn NHBoc NH 2 NHBoc N
Page 264 and 265:
RCHO BocNHOH R 2 + + O N R1 − PhS
Page 266 and 267:
BzlOOC + NH3 Cl i OH BzlO Cl Cl Bzl
Page 268 and 269:
Table 2.12 Addition a of 2-lithiofu
Page 270 and 271:
H 2N O BnO O OH O CO2H H2N O N H OH
Page 272 and 273:
353 b a BnO BnO 354 Bn N CHO OBn b
Page 274 and 275:
Table 2.13 Addition of organolithiu
Page 276 and 277:
R N O Cl 367 −O + N Bu t LDA, THF
Page 278 and 279:
HO HO OH N N • Ph • O OH O HO P
Page 280 and 281:
RO2C N O X • N O • N O N O •
Page 282 and 283:
N O 373 N O a 374, 376, 377 R2 376
Page 284 and 285:
+ N O − HN HO O R1 S R2 R3 + Ph 1
Page 286 and 287:
+ R 1 N R2 O O R 1 N R 2 − R 1 R
Page 288 and 289:
NITRONE REACTIONS 273 Table 2.14 Sy
Page 290 and 291:
+ Ph N O − Bn + O Et 3SiO MeO O H
Page 292 and 293:
O O O N Pri OCOPh R Me Bn CO 2H NHC
Page 294 and 295:
N O OBu t N O THF,−78°C, 1 h OBu
Page 296 and 297:
O O O O 292 O H N −O + Bn O HO N
Page 298 and 299:
NITRONE REACTIONS 283 The reaction
Page 300 and 301:
O − O O BnO O O + O − O − N P
Page 302 and 303:
R 1 R 2 NH 2 COOH Br a: b: c: d: e:
Page 304 and 305:
NITRONE REACTIONS 289 2.6.6.1.11. N
Page 306 and 307:
NITRONE REACTIONS 291 Nucleophilic
Page 308 and 309:
O − O O + NBoc− O NBoc N Bn 1.
Page 310 and 311:
NITRONE APPLICATION IN RADICAL POLY
Page 312 and 313:
REACTIONS OF DIPOLAR 1,3-CYCLOADDIT
Page 314 and 315:
Page 316 and 317:
Page 318 and 319:
a b c d REACTIONS OF DIPOLAR 1,3-CY
Page 320 and 321:
R REACTIONS OF DIPOLAR 1,3-CYCLOADD
Page 322 and 323:
Page 324 and 325:
a REACTIONS OF DIPOLAR 1,3-CYCLOADD
Page 326 and 327:
Page 328 and 329:
− REACTIONS OF DIPOLAR 1,3-CYCLOA
Page 330 and 331:
Page 332 and 333:
Page 334 and 335:
Page 336 and 337:
Page 338 and 339:
Page 340 and 341:
Page 342 and 343:
Page 344 and 345:
Page 346 and 347:
(a) REACTIONS OF DIPOLAR 1,3-CYCLOA
Page 348 and 349:
O HO REACTIONS OF DIPOLAR 1,3-CYCLO
Page 350 and 351:
Page 352 and 353:
Bn REACTIONS OF DIPOLAR 1,3-CYCLOAD
Page 354 and 355:
Page 356 and 357:
CO 2Me O O REACTIONS OF DIPOLAR 1,3
Page 358 and 359:
Page 360 and 361:
Page 362 and 363:
Page 364 and 365:
H H REACTIONS OF DIPOLAR 1,3-CYCLOA
Page 366 and 367:
Page 368 and 369:
Page 370 and 371:
Page 372 and 373:
Page 374 and 375:
Me REACTIONS OF DIPOLAR 1,3-CYCLOAD
Page 376 and 377:
Page 378 and 379:
Page 380 and 381:
Page 382 and 383:
O REACTIONS OF DIPOLAR 1,3-CYCLOADD
Page 384 and 385:
Page 386 and 387:
Page 388 and 389:
Ph Ph REACTIONS OF DIPOLAR 1,3-CYCL
Page 390 and 391:
− O Me REACTIONS OF DIPOLAR 1,3-C
Page 392 and 393:
Page 394 and 395:
Page 396 and 397:
Ph REACTIONS OF DIPOLAR 1,3-CYCLOAD
Page 398 and 399:
Page 400 and 401:
B C A Closed [5,6] adduct B B KINUG
Page 402 and 403:
KINUGASA REACTION ([2 + 2] CYCLOADD
Page 404 and 405:
O O N N N O R R O O L 1 : N N N 1 m
Page 406 and 407:
R 1 R 1 O + N 774 a-e Δ O N N Ph 1
Page 408 and 409:
783 784 + N O + CH3 − N O Ph CH3
Page 410 and 411:
R 1 NHOH 793 + R 2 CHO 794 Hydroxyl
Page 412 and 413:
REACTIONS WITH CYCLOPROPANES 397 O
Page 414 and 415:
REFERENCES 399 properties and synth
Page 416 and 417:
REFERENCES 401 (d) Mottley C, Mason
Page 418 and 419:
REFERENCES 403 46. Sankuratri N, Ja
Page 420 and 421:
REFERENCES 405 105. Saladino R, Ner
Page 422 and 423:
REFERENCES 407 159. Sridharan V, Mu
Page 424 and 425:
REFERENCES 409 205. Cupone G, De Ni
Page 426 and 427:
REFERENCES 411 259. Balasundaram B,
Page 428 and 429:
REFERENCES 413 310. (a) Cicchi S, M
Page 430 and 431:
REFERENCES 415 (b) Creary X. Acc. C
Page 432 and 433:
REFERENCES 417 410. Dziembowska T,
Page 434 and 435:
REFERENCES 419 459. Bourquet E, Ban
Page 436 and 437:
REFERENCES 421 Papers of 6-th Inter
Page 438 and 439:
REFERENCES 423 573. Ok D, Fisher MH
Page 440 and 441:
REFERENCES 425 636. (a) Jost S, Gim
Page 442 and 443:
REFERENCES 427 690. Haire DL, Janze
Page 444 and 445:
REFERENCES 429 721. Manzoni L, Aros
Page 446 and 447:
REFERENCES 431 762. Baldwin JE, Adl
Page 448 and 449:
REFERENCES 433 808. Leggio A, Liguo
Page 450 and 451:
3 Nitronates SEMA L. IOFFE N. D. Ze
Page 452 and 453:
SYNTHESIS OF NITRONATES 437 as O-nu
Page 454 and 455:
SYNTHESIS OF NITRONATES 439 These r
Page 456 and 457:
SYNTHESIS OF NITRONATES 441 It shou
Page 458 and 459:
X-C(NO 2) 3 NO 2-C(NO 2) 3 R R′ C
Page 460 and 461:
R R′ X NO 2 base −H + R R′ X
Page 462 and 463:
Br NaNO 2/DMF Cl R 6 R=C6H5; CO2MeR
Page 464 and 465:
OH NO 2 R EtO2CN NCO 2Et PPh 3, ben
Page 466 and 467:
NO 2 O Me R 2 R 1 PhSH Et 3N cat. M
Page 468 and 469:
R R O OAc 19 Mn III −H + NO2 Me M
Page 470 and 471:
Ag[ArC(NO2)2] 26 heptane 100°, 50
Page 472 and 473:
NO2CH=C(NO2)Ph [RR′CN 2 28 RR′C
Page 474 and 475:
Me O 2N Me O 2N 29a Br EtO 2CC CCO
Page 476 and 477:
SYNTHESIS OF NITRONATES 461 (39) (s
Page 478 and 479:
SYNTHESIS OF NITRONATES 463 In the
Page 480 and 481:
R 1 R R 2 NO 2 + R 5 R 3 42 43 R 6
Page 482 and 483:
O O N R + R"CO NO2 R′ N 42 43c Ph
Page 484 and 485:
SYNTHESIS OF NITRONATES 469 3.2.2.3
Page 486 and 487:
R R′ C R H C R′ NO2 [RR′C(NO2
Page 488 and 489:
Table 3.1 The silylation of AN by E
Page 490 and 491:
SYNTHESIS OF NITRONATES 475 Table 3
Page 492 and 493:
O Me 2RSi NMe 2 + − Me2N=C—OSiM
Page 494 and 495:
SYNTHESIS OF NITRONATES 479 decompo
Page 496 and 497:
A G N R O N H O O A Si R 1 RR 1 C=N
Page 498 and 499:
NO2CH2CH2CH2CO2ME Me CO2Me NO2CH CH
Page 500 and 501:
SYNTHESIS OF NITRONATES 485 than 20
Page 502 and 503:
R 1 R 2 LDA THF, −78°C R 1 O OLi
Page 504 and 505:
O R 1 N 51o-t OSiMe2R 3 R 2 PRINCIP
Page 506 and 507:
MeO2C H PRINCIPAL PHYSICOCHEMICAL D
Page 508 and 509:
PRINCIPAL PHYSICOCHEMICAL DATA AND
Page 510 and 511:
R' R PRINCIPAL PHYSICOCHEMICAL DATA
Page 512 and 513:
Table 3.8 (continued) PRINCIPAL PHY
Page 514 and 515:
Page 516 and 517:
Page 518 and 519:
Page 520 and 521:
Page 522 and 523:
Page 524 and 525:
Page 526 and 527:
Page 528 and 529:
** NO2 O O N O * N SiMe3 O PRINCIPA
Page 530 and 531:
Page 532 and 533:
XO R 1 N O H XO O N R R 2 = H R 3 X
Page 534 and 535:
EtO 2CCH N(O)OMe Δ or HCl NH3 / Me
Page 536 and 537:
R 1 R 2 OSi N O E—Nu R 1 R 2 REAC
Page 538 and 539:
O OM R′ N 113 R′′ Me 3SiX −
Page 540 and 541:
O O R 1 R 1 N N OSi R 2 OSi R 2 + M
Page 542 and 543:
R 1 PhO2S R 1 PhO 2S N NO2 O OSiMe
Page 544 and 545:
R 3 R 1 O R 4 R 3 R 3 R 1 R 1 55%-7
Page 546 and 547:
RR′C N MeOCO MeO C O OBEt 2 N O O
Page 548 and 549:
REACTIVITY OF NITRONATES 533 Yields
Page 550 and 551:
RO R 4 R 3 R 2 O N R 1 O P(OAlk) 3
Page 552 and 553:
REACTIVITY OF NITRONATES 537 Second
Page 554 and 555:
MeO2C Ph CO2Me O N O X 1 X 2 Ph H R
Page 556 and 557:
R CO2Me TiCl 4 reflux, overnight N
Page 558 and 559:
Me NO2 + Ph Me NO 2 Ph + Bu n O Bu
Page 560 and 561:
R R O2N O2N O N Regioselectivity +
Page 562 and 563:
REACTIVITY OF NITRONATES 547 Ref.33
Page 564 and 565:
REACTIVITY OF NITRONATES 549 Ref.52
Page 566 and 567:
MeO2C MeO 2C 160 N O OMe R OMgBr r.
Page 568 and 569:
R N O N O R N O N O Y Z X xylene, r
Page 570 and 571:
REACTIVITY OF NITRONATES 555 O N O
Page 572 and 573:
RCH2NO2 RHC N RHC N O OH Ac 2O/AcON
Page 574 and 575:
PhCOCH2SCHR′R′′ 180 R′R′
Page 576 and 577:
REACTIVITY OF NITRONATES 561 Both o
Page 578 and 579:
R 185 + R′ 195 NO2 OH ( )n KH; TH
Page 580 and 581:
NaNO2 AcOH 199 200 (+) -citronellen
Page 582 and 583:
O X X X X S 208 D F E SiMe3 NO 2 O
Page 584 and 585:
R′ R′′ HO R O N 213 O ClSi R
Page 586 and 587:
R SiO R AlkO N N R′′ O + R′
Page 588 and 589:
R′ R′ R′ R′ O N OSi 229 OH
Page 590 and 591:
R′′ OH Si - Me2Bu t Si R′ R N
Page 592 and 593:
R = Me R′ = Ph(86%);CO2Me(28%) O
Page 594 and 595:
R′O HO OR′ R′′ R′ O N * *
Page 596 and 597:
REACTIVITY OF NITRONATES 581 orient
Page 598 and 599:
REACTIVITY OF NITRONATES 583 isomer
Page 600 and 601:
O N O 249a-g + R′ 250a,b R O N O
Page 602 and 603:
REACTIVITY OF NITRONATES 587 Experi
Page 604 and 605:
BuO R 1 Me Me Me Et Et Et Me * ** O
Page 606 and 607:
REACTIVITY OF NITRONATES 591 3.4.4.
Page 608 and 609:
N N OH HO H H H HO (−)-hastinecin
Page 610 and 611:
REACTIVITY OF NITRONATES 595 compli
Page 612 and 613:
Four component [4+2] [4+2] [4+2] do
Page 614 and 615:
Bn O O REACTIVITY OF NITRONATES 599
Page 616 and 617:
Me2Si R 1 NO2 R 1 R 2 R 2 291 O EtO
Page 618 and 619:
O 2N R * = EtO + 296 OEt R * OAc Et
Page 620 and 621:
G * OH G * O G * OH: 305 306 OH Ph
Page 622 and 623:
SILYLATION OF NITRO COMPOUNDS AS A
Page 624 and 625:
RCH2CH2CHNO2 319 H a B − BH + SIL
Page 626 and 627:
R 1 R 2 Ph R2 R1 O N OSi NO2 R2 R1
Page 628 and 629:
Page 630 and 631:
Me 2N CH 2 N OSiMe 3 R 1 R 2 + O N
Page 632 and 633:
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:
Page 640 and 641:
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 646 and 647:
Page 648 and 649:
R O N OX SILYLATION OF NITRO COMPOU
Page 650 and 651:
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 656 and 657:
Page 658 and 659:
Page 660 and 661:
Page 662 and 663:
# N CO2Me OSi OMe SiO N CO2Me OSi S
Page 664 and 665:
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 674 and 675:
Page 676 and 677:
Page 678 and 679:
Page 680 and 681:
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 686 and 687:
X R 1 434 R 2 R 1 432 X + A NO 2 R
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 692 and 693:
Page 694 and 695:
R 2 SILYLATION OF NITRO COMPOUNDS A
Page 696 and 697:
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 702 and 703:
Page 704 and 705:
RN(NO2)SiMe3 RN N + 473a,b OSiMe3 i
Page 706 and 707:
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 714 and 715:
Page 716 and 717:
Me Me Me Me Me Me Ph eq O 507a Ph N
Page 718 and 719:
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 728 and 729:
Page 730 and 731:
Page 732 and 733:
Page 734 and 735:
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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