Handbook of Functionalized Organometallics Applications in S

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12.3 Functionalized Organotitanium Derivatives the titanated ester portion (methyl or ethyl ester ynoate is followed by a second ring closure at the carbonyl moiety) as described in Scheme 12.67 [86]. Me 3Si Scheme 12.67 SiMe 3 CO 2Bu-t Ti(OPr-i) 2 CO 2Bu-t SiMe 3 1. i-PrOD 2. H + CO 2Bu-t This type of cyclization of ethyl ester dienolates provides bicyclic ketones and was recently used for the preparation of carbacycline [87]. EtO EtO 2C O CHO H 11C 5 EtO2C EtO 2C Scheme 12.68 HO H H Ti(OPr-i) 4 2 i-PrMgCl Et2O C 5H 11 H O EtO 2C X 3Ti TiO C 5H 11 O OEt Carbacycline CO 2Et Ti(OPr-i) 2 D 84% 537
538 12 Functionalized Organozirconium and Titanium in Organic Synthesis References 1 Titanium and Zirconium in Organic Synthesis, Ed. I. Marek, Wiley-VCH, Weinheim, 2002 2 Original preparation of Cp 2Zr(H)Cl was reported by: Wailes, H. Weijold, J. Organomet. Chem., 1970, 24, 405. Pioneer synthetic application: J.A. Labinger, D. W. Hart, E. E. Seibert, J. Schwartz, J. Am. Chem. Soc., 1975, 97, 679 3 J. Schwartz, M. L. Loots, H. Kosugi, J. Am. Chem. Soc., 1980, 102, 1333 4 B. H. Lipshutz, R. Keil, E. L. Ellsworth, Tetrahedron Lett., 1990, 31, 7257 5 a) B. H. Lipshutz, R. Keil, J. Am. Chem. Soc., 1992, 114, 7919 b) B. H. Lipshutz, M. R. Wood, J. Am. Chem. Soc., 1994, 116, 11689 c) D. R. Swanson, T. Nguyen, Y. Nodal, E. Negishi, J. Org. Chem., 1991, 56, 2590 6 P. Wipf, W. Xu, J. Org. Chem., 1993, 58, 825 7 P. Wipf, W. Xu, Tetrahedron Lett., 1994, 35, 5197 8 P. Wipf, P. D. G. Coish Tetrahedron Lett., 1997, 38, 5073 9 P. Wipf, W. Xu, H. Takahashi, H. Jahn, P. D. G. Coish, Pure Appl. Chem., 1997, 69, 689 10 P. Wipf, P. D. G. Coish, J. Org. Chem., 1999, 64, 5053 11 (a) P. Wipf, W. Xu, H. Takahashi, H. Jahn, P. D. G. Coish, J. Org. Chem., 1998, 63, 6454 (b) P. Wipf, C. Kendall, Chem. Eur. J., 2002,8, 1779 12 B. H. Lipshutz, R. Keil, Inorg. Chem. Acta., 1994, 220,41 13 B. H. Lipshutz, C.Lindsley, A. Blandari, Tetrahedron Lett., 1994, 35, 4669 14 P. Wipf, W. Xu, Synlett, 1992, 718 15 (a) P. Wipf, C. Kendall, C. J. Stephenson, J. Am. Chem. Soc., 2001, 123, 5122 (b) P. Wipf, C. Kendall, C. J. Stephenson, J. Am. Chem. Soc., 2003, 125, 761 16 P. Wipf, C. Kendall, Org. Lett., 2001, 3, 2773 17 P. Wipf, R. L. Nunes, Tetrahedron, 2004, 60, 1269 18 D. E. Chaves, E. N. Jacobsen, Angew. Chem. Int. Ed., 2001, 40, 3667 19 D. Trauner, J. B. Schwarz, S. J. Danishefski, Angew. Chem. Int. Ed., 1999, 38, 3542 20 P. Wipf, W. Xu, J. H. Smitrovich, R. Lehman, L. M. Venanzi, Tetrahedron, 1994, 50, 1935 21 B. Zheng, M. Srebnik, J. Org. Chem., 1995, 60, 1912 22 S. Pereira, B. Zheng, M. Srebnik, J. Org. Chem., 1995, 60, 6260 23 J. T. Wang, Y. W. Zhang, Y. M. Xu, G. C. Bai, Youji Huaxue, 1989, 9,41 24 S. Harada, N. Kowase, T. Taguchi, Y. Hanzawa Tetrahedron Lett., 1997, 38, 1957 25 S. Harada, N. Kowase, N. Taguchi, Y. Dobashi, A. Dobashi, Y. Hanzawa, Tetrahedron, 1998, 54, 753 26 H. Makase, E. Negishi Eur. J. Org. Chem., 1999, 969 27 a) C. A. Bertelo, J. Schwartz, J. Am. Chem. Soc., 1975, 97, 228 b) J. A. Labinger, D. W. Hart, W. E. Scibert, J. Schwartz, J. Am. Chem. Soc., 1975, 97, 3851 28 S. L. Buchwald, Q. Fang, S. M. King, Tetrahedron Lett., 1988, 29, 3445 29 S. Harada, T. Taguchi, N. Tabuchi, K. Narita, Y. Hanzawa, Angew. Chem. Int. Ed, 1998, 37, 1696 30 A. Kakuuchi, T. Taguchi, Y. Hanzawa, Tetrahedron Lett., 2001, 42, 1547 31 A. Kakuuchi, T. Taguchi, Y. Hanzawa, Eur. J. Org. Chem., 2003, 116 32 Y. Hanzawa, N. Tabuchi, T. Taguchi Tetrahedron Lett., 1998, 39, 6249 33 Y. Hanzawa, N. Tabuchi, T. Taguchi Tetrahedron Lett., 1998, 39, 8141 34 Y. Hanzawa, N. Tabuchi, K. Saito, S. Noguchi, T. Taguchi, Angew. Chem. Int. Ed., 1999, 38, 2395 35 Y. Hanzawa, A. Kakuuchi, M. Yabe, K. Narita, N. Taguchi, T. Taguchi, Tetrahedron Lett., 2001, 42, 1737 36 Y. Hanzawa, K. Narita, T. Taguchi, Tetrahedron Lett., 2000, 41, 109 37 Y. Hanzawa, K. Narita, M. Yabe, T. Taguchi, Tetrahedron, 2002, 58,10429 38 Y. Hanzawa, K. Narita, T. Taguchi, Tetrahedron Lett., 2000, 41, 109 39 A. M. Sun, X. Huang, Tetrahedron, 1999, 55, 13201
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Organometallics. Paul Knochel Copyr
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Handbook of Functionalized Organome
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Contents Preface XV List of Authors
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Contents 3.3.9 Oxidation of Functio
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6.3.1 Nucleophilic Addition onto Ca
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9.2.3 Preparation of Functionalized
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13.6.4 Nickel-Catalyzed Cross-coupl
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Preface Since the pioneering work o
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XVIII List of Authors Corinne Gosmi
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1 Introduction Paul Knochel and Fel
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umorganic is directly generated in
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Et H 21 Et AlBu 2 + CO 2Et Cu(CN)Mg
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8 2 Polyfunctional Lithium Organome
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10 2 Polyfunctional Lithium Organom
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R R 12 2 Polyfunctional Lithium Org
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MeO MeO R 14 2 Polyfunctional Lithi
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N 16 2 Polyfunctional Lithium Organ
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Li LiO 20 2 Polyfunctional Lithium
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Li 22 2 Polyfunctional Lithium Orga
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26 Ph O Ni-Pr 2 2 Polyfunctional Li
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28 Li 2 Polyfunctional Lithium Orga
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Li 32 203 2 Polyfunctional Lithium
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36 Br 2 Polyfunctional Lithium Orga
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3 Functionalized Organoborane Deriv
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Br SSiMe 2tBu 4 3.2 Preparation and
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B O O 3.2 Preparation and Reaction
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3.2 Preparation and Reaction of Fun
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Ar H Ar = O HB O CF 3 CF 3 3.2 Prep
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X X Cl Cl TfO Cl 3.2 Preparation an
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HO HO Br OH O X N N O N 3.2 Prepara
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MOMO MOMO I CbzN O 3.2 Preparation
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(HO) 3B O NMe 3 N N O Br 3.2 Prepar
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H H O O N H N H O OEt O O OEt O 3.2
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t BuO2C O N H 3.2 Preparation and R
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R H2O R R B(OH) 2 B(OH) 2 3.3 Prepa
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3.3 Preparation and Reactions of Fu
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R 124 BF 3K Br 3.3 Preparation and
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B O O I OR O OR O O O O O OR 3.3 Pr
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S N O B O I O 133 3.4 Preparation a
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3.5 Synthesis and Reactions of Func
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R TrocO S N R 1 O S N 13 12 O 1 160
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22 H. Nakamura, M. Fujiwara, Y. Yam
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102 K. A. Scheidt, A. Tasaka, T. D.
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4 Polyfunctional Magnesium Organome
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crystallize with four-coordinated M
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4.2Methods of Preparation of Grigna
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NC Br Br 4.2Methods of Preparation
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N N Ph I 4.2Methods of Preparation
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Cl MgBr 4.2Methods of Preparation o
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O O O O 4.2Methods of Preparation o
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O Me Me O Pent I 4.2Methods of Prep
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4.3 Further Applications of Functio
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OTIPS I iPrMgCl OTIPS 4.3 Further A
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4.4 Application of Functionalized M
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I O O OBn Pd(t-Bu 3P) 2 (10 mol%) 4
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Me OTf CO2Et + Me 4.4 Application o
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12 a) F. Bickelhaupt in H. G. Riche
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56 G. Varchi, C. Kofink, D. M. Lind
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kin Trans. 1 1992, 1393; b) M. Sato
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31, 805; J. F. Hartwig, Angew. Chem
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5 Polyfunctional Silicon Organometa
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stereocontrol [5]. Similar chiral c
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5.2 Allylic Silanes seven-membered
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SiMe 3 33 Pr OH OSiMe 3 SiMe 3 34 O
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5.2 Allylic Silanes Although alkyl
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R O Si H 60a (R = H) 60b (R = Me) R
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Bpin SiMe 2Ph (CH 2) 2Ph 73 EtCH(OE
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BnO HO SiMe2Ph 2 BnO CHO BnO O BF3
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5.3 Alkenylsilanes When the same st
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HO I O Si Mo cat. : m n I O Si 111
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5.4Alkylsilanes Transition metal-ca
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5.4Alkylsilanes The fluoride-induce
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5.5 Miscellaneous Preparations and
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5.5 Miscellaneous Preparations and
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716. (c)I. E. Markó, J.-M. Planche
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6 Polyfunctional Tin Organometallic
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phine ligand or Pd II (PPh 3) 2Cl 2
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Bu 3 Sn Scheme 6.4 n-Pent + Me I O
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N N N H 2 I Scheme 6.8 N + Me Sn 3
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O O O NaO HO Me P O OH O OH (+)-Fos
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6.2 Metal-Catalyzed Coupling Reacti
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6.2 Metal-Catalyzed Coupling Reacti
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6.3 Nucleophilic Additions a-hydrox
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6.3 Nucleophilic Additions oxy alde
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6.3 Nucleophilic Additions found ap
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6.3 Nucleophilic Additions 6.3.1.5.
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6.3 Nucleophilic Additions ethylami
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N H 91% (ee:84%) Scheme 6.31 N CO 2
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6.4 Radical Reactions of Organotins
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TsN Scheme 6.37 + Bu 3Sn O Ph AIBN
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6.5.2 Tin-to-lithium Exchange 6.5.2
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Ar OR Scheme 6.42 N H SnBu 3 n-BuLi
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References 1 D. Azarian, S. S. Dua,
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Commun., 2002, 2608±2609; W. Su, S
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110 Y. Obora, M. Nakanishi, M. Toku
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178 Y. Yamamoto, H. Yatagai, Y. Nar
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J. Chem. Soc., Chem. Commun., 1995,
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301 D. P. G. Hamon, R. A. Massy-Wes
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371 I. D. Gridnev, O. L. Tok, N. A.
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252 7 Polyfunctional Zinc Organomet
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BnO H Me 37 :1:1mixtureof diastereo
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262 Me 3Si 7 Polyfunctional Zinc Or
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264 F F 7 Polyfunctional Zinc Organ
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Bu S O IZn(CH 2) 4ZnI 94 268 7 Poly
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OAc MeO I EtO 2C 272 CHO S C N 7 Po
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276 O 7 Polyfunctional Zinc Organom
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280 E 7 Polyfunctional Zinc Organom
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282 MeO 2C O I 7 Polyfunctional Zin
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H Ph 284 7 Polyfunctional Zinc Orga
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288 Ph N 214 O 7 Polyfunctional Zin
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294 IZn AcO 7 Polyfunctional Zinc O
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O 310 7 Polyfunctional Zinc Organom
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318 AcO 7 Polyfunctional Zinc Organ
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EtO 2C 320 MeO 7 Polyfunctional Zin
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MeO O 322 n-Hept O O I Me 7 Polyfun
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MeO 462 324 460 Br I 463 7 Polyfunc
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348 8 Polyfunctional 1,1-Organodime
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350 O 8 Polyfunctional 1,1-Organodi
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CH 2(ZnI) 2 4 362 8 Polyfunctional
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9 Polyfunctional Organocopper Reage
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S 5 CuI·LiCl Cu(CN)Li Li naphthale
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Br CO 2Et I CO 2Et CO 2Et Np 2CuLi
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9.2 Preparation of Functionalized O
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Pent I O O Pent I CO 2Et O Br Pent
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Ph Ph N OMe 1) n-BuLi 2) alkynylcop
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9.3 Applications of Functionalized
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PrCu·MgBr 2·SMe 2 Pr Me H Pr H HO
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19 X. Yang, T. Rotter, C. Piazza, P
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n-C 7H 15 398 10 Functional Organon
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400 10 Functional Organonickel Reag
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O 424 10 Functional Organonickel Re
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TIPSO R 1 Cp 2ClZr O H 426 O N 10 F
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O 438 O Br 10 Functional Organonick
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Cl 442 CN 10 Functional Organonicke
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11 Polyfunctional Metal Carbenes fo
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11.2 Chromium-Templated Cycloadditi
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11.2 Chromium-Templated Cycloadditi
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(CO) 5Cr O Ph 15 1) t Bu t BuOMe, 5
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O MeO O O O O MeO O OMe Cr(CO) 5 Me
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11.2.3 Cyclization of Chromium Olig
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(CO)5Cr OR * O S + OMe 11.2 Chromiu
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[2+2+1] R 1 R 1 OH (CO) 5Cr R 2 (CO
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11.3 Reactions of Higher Nuclearity
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Br O X Br O R 2 R 2 O 85: X = Si-tB
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11.3 Reactions of Higher Nuclearity
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11.4 Metathesis Reactions Catalyzed
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R 2 R 1 O R O 3 O 11.4 Metathesis R
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i Pr i Pr i Pr Me Me (R)-160 Ph O O
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11.5 Transmetallation The dimerizat
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11.6 Metal Carbenes in Peptide Chem
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11.7 Stereoselective Syntheses with
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11.7 Stereoselective Syntheses with
Page 500 and 501: 11.7 Stereoselective Syntheses with
Page 506 and 507: O O O O 100% H 2N O O O O O 311a Cr
Page 508 and 509: 11.8 Sugar Metal Carbenes as Organo
Page 510 and 511: References zation reactions that al
Page 512 and 513: 35 (a) C.A. Merlic, Y. You, D.M. Mc
Page 514 and 515: D. R. Cefalo, P. J. Bonitatebus Jr.
Page 516 and 517: 12 Functionalized Organozirconium a
Page 518 and 519: 12.2 Functionalized Organozirconoce
Page 520 and 521: Ph O (H)ZrCp Ph O 2Cl Ph O O O 92 %
Page 524 and 525: i-PrO O OBu-t O H N Scheme 12.15 H
Page 526 and 527: BnO Scheme 12.19 O BnO + 27 28 Cp 2
Page 530 and 531: R 1 O O O R R1 R 2 Scheme 12.28 R P
Page 534 and 535: 12.3 Functionalized Organotitanium
Page 538 and 539: t-BuOOC Scheme 12.44 O CH 3 7.5 mol
Page 542 and 543: H 13C 6 O R Scheme 12.52 SiMe 3 O T
Page 546 and 547: O O OEt 87 Scheme 12.59 Scheme 12.6
Page 552 and 553: 40 A. M. Sun, X. Huang, Heteroatom
Page 554 and 555: 13 Manganese Organometallics for th
Page 556 and 557: 13.2.2 Preparation of Organomangane
Page 558 and 559: 13.3 1,2-Addition to Aldehydes and
Page 560 and 561: 13.3.2 Manganese-Mediated Barbier-
Page 562 and 563: HeptMnX + HeptMnX + Scheme 13.17 Cl
Page 564 and 565: 13.4 Preparation of Ketones by Acyl
Page 566 and 567: Me 3Si Cl ( ) 3 R Li 80% 82% Scheme
Page 568 and 569: 13.5 1,4-Addition of Organomanganes
Page 570 and 571: BuM BuMgCl BuMnCl BuMgCl BuCu BuCu
Page 572 and 573: 13.6 Transition-Metal-Catalyzed Cro
Page 574 and 575: 13.6 Transition-Metal-Catalyzed Cro
Page 576 and 577: I Cl Scheme 13.56 MeO MnCl (1.2 equ
Page 578 and 579: 13.7 Manganese-Mediated Cross-coupl
Page 580 and 581: 13 C. Boucley, G. Cahiez, unpublish
Page 582 and 583: 570 14 Polyfunctional Electrophilic
Page 586 and 587: η5 η6 η4 η7 574 14 Polyfunction
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588 14 Polyfunctional Electrophilic
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51 594 CO 2Me + Fe(CO)3 CO2Me 14 Po
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Table 14.1 Examples of synthetic ap
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602 Entry Target molecule Disconnec
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Entry Target molecule Disconnection
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Page 622 and 623:
Target molecule Disconnections Mult
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15 Polyfunctional Zinc, Cobalt and
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Trifluoromethylzinc compounds prepa
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15.3 Electrochemical Synthesis and
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15.3.2 Carbon±Carbon Bond Formatio
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Cl Cl NC + MeO2C 1eq 2eq e, CoX 2 c
Page 650 and 651:
1eq Br FG + R 2eq OAc e, CoX 2 cat
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Cl O + O e, FeBr 2(Bpy) n DMF, Fe a
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15.4 Electrosynthesis of Compounds
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Page 658 and 659:
FG CuCN/LiCl ZnBr 0ºC CuZnBrCN 15.
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15.5 General Conclusion (industrial
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17 Durandetti, M.; Devaud, M.; Peri
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I2 Index b-alkoxyalkylidenemalonic,
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I4 Index boronic ester 47 4-boronyl
Page 670 and 671:
I6 Index cyclohexadiene 415 cyclohe
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I8 Index fluoroalkenylstannane 206
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I10 Index iron-catalyzed carbolithi
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I12 Index nickel-catalyzed carbozin
Page 678 and 679:
I14 Index psicosecarbene complexes
Page 680 and 681:
I16 Index Suzuki-Miyaura reaction a
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