Di(isopropylprenyl)borane: A new hydroboration reagent for the synthesis of alkyl and alkenyl boronic acids

Angewandte Chemie - International Edition

Volumn 42, Issue 29, 2003, Pages 3399-3404

  Kalinin, Alexey V ^a   Scherer, Stefan ^b   Snieckus, Victor ^c  

^a UNIVERSITY OF WATERLOO   (Canada)

^b CLARIANT PRODUKTE DEUTSCHLAND GMBH   (Germany)

^c QUEEN S UNIVERSITY   (Canada)

Author keywords

Boranes; Cross coupling; Homogeneous catalysis; Hydroboration

Indexed keywords

HYDROLYSIS; INORGANIC ACIDS; OXIDATION; SYNTHESIS (CHEMICAL);

HYDROBORATION;

BORON COMPOUNDS;

ALKENYL GROUP; ALKYL GROUP; BIS(ISOPROPYLPRENYL)BORANE; BORANE DERIVATIVE; BORONIC ACID DERIVATIVE; CARBONYL DERIVATIVE; DISIAMYLBORANE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; HYDROBORATION; HYDROLYSIS; OXIDATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0041528503     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351312     Document Type: Article

References (118)

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20. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483; A. Suzuki in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 49-97; A. Suzuki, J. Organomet. Chem. 2002, 653, 83-90; N. Miyaura, Top. Curr. Chem. 2002, 219, 11-59; K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169-196; G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893-895; G. A. Molander, M. R. Rivero, Org. Lett. 2002, 4, 107-109; J. H. Kirchhoff, C. Dai, G. C. Fu, Angew. Chem. 2002, 114, 2025-2027; Angew. Chem. Int. Ed. 2002, 41, 1945-1947; J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G.C. Fu, J. Am. Chem. Soc. 2002, 124, 13662-13663; N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553-5566; J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162-1163; C. Bolm, J. P. Hildebrand, K. Muñiz, N. Hermanns, Angew. Chem. 2001, 113, 3382-3407; Angew. Chem. Int. Ed. 2001, 40, 3284-3308; S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001,113, 4676-4701; Angew. Chem. Int. Ed. 2001, 40, 4544-4568.
21. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483; A. Suzuki in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 49-97; A. Suzuki, J. Organomet. Chem. 2002, 653, 83-90; N. Miyaura, Top. Curr. Chem. 2002, 219, 11-59; K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169-196; G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893-895; G. A. Molander, M. R. Rivero, Org. Lett. 2002, 4, 107-109; J. H. Kirchhoff, C. Dai, G. C. Fu, Angew. Chem. 2002, 114, 2025-2027; Angew. Chem. Int. Ed. 2002, 41, 1945-1947; J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G.C. Fu, J. Am. Chem. Soc. 2002, 124, 13662-13663; N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553-5566; J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162-1163; C. Bolm, J. P. Hildebrand, K. Muñiz, N. Hermanns, Angew. Chem. 2001, 113, 3382-3407; Angew. Chem. Int. Ed. 2001, 40, 3284-3308; S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001,113, 4676-4701; Angew. Chem. Int. Ed. 2001, 40, 4544-4568.
22. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483; A. Suzuki in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 49-97; A. Suzuki, J. Organomet. Chem. 2002, 653, 83-90; N. Miyaura, Top. Curr. Chem. 2002, 219, 11-59; K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169-196; G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893-895; G. A. Molander, M. R. Rivero, Org. Lett. 2002, 4, 107-109; J. H. Kirchhoff, C. Dai, G. C. Fu, Angew. Chem. 2002, 114, 2025-2027; Angew. Chem. Int. Ed. 2002, 41, 1945-1947; J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G.C. Fu, J. Am. Chem. Soc. 2002, 124, 13662-13663; N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553-5566; J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162-1163; C. Bolm, J. P. Hildebrand, K. Muñiz, N. Hermanns, Angew. Chem. 2001, 113, 3382-3407; Angew. Chem. Int. Ed. 2001, 40, 3284-3308; S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001,113, 4676-4701; Angew. Chem. Int. Ed. 2001, 40, 4544-4568.
23. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483; A. Suzuki in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 49-97; A. Suzuki, J. Organomet. Chem. 2002, 653, 83-90; N. Miyaura, Top. Curr. Chem. 2002, 219, 11-59; K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169-196; G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893-895; G. A. Molander, M. R. Rivero, Org. Lett. 2002, 4, 107-109; J. H. Kirchhoff, C. Dai, G. C. Fu, Angew. Chem. 2002, 114, 2025-2027; Angew. Chem. Int. Ed. 2002, 41, 1945-1947; J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G.C. Fu, J. Am. Chem. Soc. 2002, 124, 13662-13663; N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553-5566; J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162-1163; C. Bolm, J. P. Hildebrand, K. Muñiz, N. Hermanns, Angew. Chem. 2001, 113, 3382-3407; Angew. Chem. Int. Ed. 2001, 40, 3284-3308; S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001,113, 4676-4701; Angew. Chem. Int. Ed. 2001, 40, 4544-4568.
24. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483; A. Suzuki in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 49-97; A. Suzuki, J. Organomet. Chem. 2002, 653, 83-90; N. Miyaura, Top. Curr. Chem. 2002, 219, 11-59; K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169-196; G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893-895; G. A. Molander, M. R. Rivero, Org. Lett. 2002, 4, 107-109; J. H. Kirchhoff, C. Dai, G. C. Fu, Angew. Chem. 2002, 114, 2025-2027; Angew. Chem. Int. Ed. 2002, 41, 1945-1947; J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G.C. Fu, J. Am. Chem. Soc. 2002, 124, 13662-13663; N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553-5566; J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162-1163; C. Bolm, J. P. Hildebrand, K. Muñiz, N. Hermanns, Angew. Chem. 2001, 113, 3382-3407; Angew. Chem. Int. Ed. 2001, 40, 3284-3308; S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001,113, 4676-4701; Angew. Chem. Int. Ed. 2001, 40, 4544-4568.
25. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483; A. Suzuki in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 49-97; A. Suzuki, J. Organomet. Chem. 2002, 653, 83-90; N. Miyaura, Top. Curr. Chem. 2002, 219, 11-59; K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169-196; G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893-895; G. A. Molander, M. R. Rivero, Org. Lett. 2002, 4, 107-109; J. H. Kirchhoff, C. Dai, G. C. Fu, Angew. Chem. 2002, 114, 2025-2027; Angew. Chem. Int. Ed. 2002, 41, 1945-1947; J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G.C. Fu, J. Am. Chem. Soc. 2002, 124, 13662-13663; N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553-5566; J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162-1163; C. Bolm, J. P. Hildebrand, K. Muñiz, N. Hermanns, Angew. Chem. 2001, 113, 3382-3407; Angew. Chem. Int. Ed. 2001, 40, 3284-3308; S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001,113, 4676-4701; Angew. Chem. Int. Ed. 2001, 40, 4544-4568.
26. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483; A. Suzuki in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 49-97; A. Suzuki, J. Organomet. Chem. 2002, 653, 83-90; N. Miyaura, Top. Curr. Chem. 2002, 219, 11-59; K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169-196; G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893-895; G. A. Molander, M. R. Rivero, Org. Lett. 2002, 4, 107-109; J. H. Kirchhoff, C. Dai, G. C. Fu, Angew. Chem. 2002, 114, 2025-2027; Angew. Chem. Int. Ed. 2002, 41, 1945-1947; J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G.C. Fu, J. Am. Chem. Soc. 2002, 124, 13662-13663; N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553-5566; J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162-1163; C. Bolm, J. P. Hildebrand, K. Muñiz, N. Hermanns, Angew. Chem. 2001, 113, 3382-3407; Angew. Chem. Int. Ed. 2001, 40, 3284-3308; S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001,113, 4676-4701; Angew. Chem. Int. Ed. 2001, 40, 4544-4568.
27. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483; A. Suzuki in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 49-97; A. Suzuki, J. Organomet. Chem. 2002, 653, 83-90; N. Miyaura, Top. Curr. Chem. 2002, 219, 11-59; K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169-196; G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893-895; G. A. Molander, M. R. Rivero, Org. Lett. 2002, 4, 107-109; J. H. Kirchhoff, C. Dai, G. C. Fu, Angew. Chem. 2002, 114, 2025-2027; Angew. Chem. Int. Ed. 2002, 41, 1945-1947; J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G.C. Fu, J. Am. Chem. Soc. 2002, 124, 13662-13663; N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553-5566; J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162-1163; C. Bolm, J. P. Hildebrand, K. Muñiz, N. Hermanns, Angew. Chem. 2001, 113, 3382-3407; Angew. Chem. Int. Ed. 2001, 40, 3284-3308; S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001,113, 4676-4701; Angew. Chem. Int. Ed. 2001, 40, 4544-4568.
28. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483; A. Suzuki in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 49-97; A. Suzuki, J. Organomet. Chem. 2002, 653, 83-90; N. Miyaura, Top. Curr. Chem. 2002, 219, 11-59; K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169-196; G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893-895; G. A. Molander, M. R. Rivero, Org. Lett. 2002, 4, 107-109; J. H. Kirchhoff, C. Dai, G. C. Fu, Angew. Chem. 2002, 114, 2025-2027; Angew. Chem. Int. Ed. 2002, 41, 1945-1947; J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G.C. Fu, J. Am. Chem. Soc. 2002, 124, 13662-13663; N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553-5566; J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162-1163; C. Bolm, J. P. Hildebrand, K. Muñiz, N. Hermanns, Angew. Chem. 2001, 113, 3382-3407; Angew. Chem. Int. Ed. 2001, 40, 3284-3308; S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001,113, 4676-4701; Angew. Chem. Int. Ed. 2001, 40, 4544-4568.
29. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483; A. Suzuki in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 49-97; A. Suzuki, J. Organomet. Chem. 2002, 653, 83-90; N. Miyaura, Top. Curr. Chem. 2002, 219, 11-59; K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169-196; G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893-895; G. A. Molander, M. R. Rivero, Org. Lett. 2002, 4, 107-109; J. H. Kirchhoff, C. Dai, G. C. Fu, Angew. Chem. 2002, 114, 2025-2027; Angew. Chem. Int. Ed. 2002, 41, 1945-1947; J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G.C. Fu, J. Am. Chem. Soc. 2002, 124, 13662-13663; N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553-5566; J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162-1163; C. Bolm, J. P. Hildebrand, K. Muñiz, N. Hermanns, Angew. Chem. 2001, 113, 3382-3407; Angew. Chem. Int. Ed. 2001, 40, 3284-3308; S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001,113, 4676-4701; Angew. Chem. Int. Ed. 2001, 40, 4544-4568.
30. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483; A. Suzuki in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 49-97; A. Suzuki, J. Organomet. Chem. 2002, 653, 83-90; N. Miyaura, Top. Curr. Chem. 2002, 219, 11-59; K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169-196; G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893-895; G. A. Molander, M. R. Rivero, Org. Lett. 2002, 4, 107-109; J. H. Kirchhoff, C. Dai, G. C. Fu, Angew. Chem. 2002, 114, 2025-2027; Angew. Chem. Int. Ed. 2002, 41, 1945-1947; J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G.C. Fu, J. Am. Chem. Soc. 2002, 124, 13662-13663; N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553-5566; J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162-1163; C. Bolm, J. P. Hildebrand, K. Muñiz, N. Hermanns, Angew. Chem. 2001, 113, 3382-3407; Angew. Chem. Int. Ed. 2001, 40, 3284-3308; S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001,113, 4676-4701; Angew. Chem. Int. Ed. 2001, 40, 4544-4568.
31. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483; A. Suzuki in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 49-97; A. Suzuki, J. Organomet. Chem. 2002, 653, 83-90; N. Miyaura, Top. Curr. Chem. 2002, 219, 11-59; K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169-196; G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893-895; G. A. Molander, M. R. Rivero, Org. Lett. 2002, 4, 107-109; J. H. Kirchhoff, C. Dai, G. C. Fu, Angew. Chem. 2002, 114, 2025-2027; Angew. Chem. Int. Ed. 2002, 41, 1945-1947; J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G.C. Fu, J. Am. Chem. Soc. 2002, 124, 13662-13663; N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553-5566; J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162-1163; C. Bolm, J. P. Hildebrand, K. Muñiz, N. Hermanns, Angew. Chem. 2001, 113, 3382-3407; Angew. Chem. Int. Ed. 2001, 40, 3284-3308; S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001,113, 4676-4701; Angew. Chem. Int. Ed. 2001, 40, 4544-4568.
32. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483; A. Suzuki in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 49-97; A. Suzuki, J. Organomet. Chem. 2002, 653, 83-90; N. Miyaura, Top. Curr. Chem. 2002, 219, 11-59; K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169-196; G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893-895; G. A. Molander, M. R. Rivero, Org. Lett. 2002, 4, 107-109; J. H. Kirchhoff, C. Dai, G. C. Fu, Angew. Chem. 2002, 114, 2025-2027; Angew. Chem. Int. Ed. 2002, 41, 1945-1947; J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G.C. Fu, J. Am. Chem. Soc. 2002, 124, 13662-13663; N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553-5566; J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162-1163; C. Bolm, J. P. Hildebrand, K. Muñiz, N. Hermanns, Angew. Chem. 2001, 113, 3382-3407; Angew. Chem. Int. Ed. 2001, 40, 3284-3308; S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001,113, 4676-4701; Angew. Chem. Int. Ed. 2001, 40, 4544-4568.
33. R. B. Bedford, C. S. J. Cazin, S. J. Coles, T. Gelbrich, P. N. Horton, M. B. Hursthouse, M. E. Light, Organometallics 2003, 22, 987-999; N. R. Anastasi, K. M. Waltz, W. L. Weerakoon, J. F. Hartwig, Organometallics 2003, 22, 365-369, and references therein; D. E. Portlock, R. Ostaszewski, D. Naskar, L. West, Tetrahedron Lett. 2003, 44, 603-605; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691-1694, and references therein; G. W. Kabalka, S. K. Guchhait, Org. Lett. 2003, 5, 729-731; G. W. Kabalka, B. Venkataiah, Tetrahedron Lett. 2002, 43, 3703-3705; G. K. S. Prakash, M. Mandal, S. Schweizer, N. A. Petasis, G. A. Olah, J. Org. Chem. 2002, 67, 3718-3723; D. A. Evans, J. L. Katz, G. S. Peterson, T. Hintermann, J. Am. Chem. Soc. 2001, 123, 12411-12413; C. P. Decicco, Y. Song, D. A. Evans, Org. Lett. 2001, 3, 1029-1032; J. C. Antilla, S. L. Buchwald, Org. Lett. 2001, 3, 2077-2079; T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2000, 611, 392-402, and references therein; M. Murata, T. Oyama, S. Watanabe, Y. Masuda, J. Org. Chem. 2000, 65, 164-168.
34. R. B. Bedford, C. S. J. Cazin, S. J. Coles, T. Gelbrich, P. N. Horton, M. B. Hursthouse, M. E. Light, Organometallics 2003, 22, 987-999; N. R. Anastasi, K. M. Waltz, W. L. Weerakoon, J. F. Hartwig, Organometallics 2003, 22, 365-369, and references therein; D. E. Portlock, R. Ostaszewski, D. Naskar, L. West, Tetrahedron Lett. 2003, 44, 603-605; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691-1694, and references therein; G. W. Kabalka, S. K. Guchhait, Org. Lett. 2003, 5, 729-731; G. W. Kabalka, B. Venkataiah, Tetrahedron Lett. 2002, 43, 3703-3705; G. K. S. Prakash, M. Mandal, S. Schweizer, N. A. Petasis, G. A. Olah, J. Org. Chem. 2002, 67, 3718-3723; D. A. Evans, J. L. Katz, G. S. Peterson, T. Hintermann, J. Am. Chem. Soc. 2001, 123, 12411-12413; C. P. Decicco, Y. Song, D. A. Evans, Org. Lett. 2001, 3, 1029-1032; J. C. Antilla, S. L. Buchwald, Org. Lett. 2001, 3, 2077-2079; T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2000, 611, 392-402, and references therein; M. Murata, T. Oyama, S. Watanabe, Y. Masuda, J. Org. Chem. 2000, 65, 164-168.
35. R. B. Bedford, C. S. J. Cazin, S. J. Coles, T. Gelbrich, P. N. Horton, M. B. Hursthouse, M. E. Light, Organometallics 2003, 22, 987-999; N. R. Anastasi, K. M. Waltz, W. L. Weerakoon, J. F. Hartwig, Organometallics 2003, 22, 365-369, and references therein; D. E. Portlock, R. Ostaszewski, D. Naskar, L. West, Tetrahedron Lett. 2003, 44, 603-605; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691-1694, and references therein; G. W. Kabalka, S. K. Guchhait, Org. Lett. 2003, 5, 729-731; G. W. Kabalka, B. Venkataiah, Tetrahedron Lett. 2002, 43, 3703-3705; G. K. S. Prakash, M. Mandal, S. Schweizer, N. A. Petasis, G. A. Olah, J. Org. Chem. 2002, 67, 3718-3723; D. A. Evans, J. L. Katz, G. S. Peterson, T. Hintermann, J. Am. Chem. Soc. 2001, 123, 12411-12413; C. P. Decicco, Y. Song, D. A. Evans, Org. Lett. 2001, 3, 1029-1032; J. C. Antilla, S. L. Buchwald, Org. Lett. 2001, 3, 2077-2079; T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2000, 611, 392-402, and references therein; M. Murata, T. Oyama, S. Watanabe, Y. Masuda, J. Org. Chem. 2000, 65, 164-168.
36. R. B. Bedford, C. S. J. Cazin, S. J. Coles, T. Gelbrich, P. N. Horton, M. B. Hursthouse, M. E. Light, Organometallics 2003, 22, 987-999; N. R. Anastasi, K. M. Waltz, W. L. Weerakoon, J. F. Hartwig, Organometallics 2003, 22, 365-369, and references therein; D. E. Portlock, R. Ostaszewski, D. Naskar, L. West, Tetrahedron Lett. 2003, 44, 603-605; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691-1694, and references therein; G. W. Kabalka, S. K. Guchhait, Org. Lett. 2003, 5, 729-731; G. W. Kabalka, B. Venkataiah, Tetrahedron Lett. 2002, 43, 3703-3705; G. K. S. Prakash, M. Mandal, S. Schweizer, N. A. Petasis, G. A. Olah, J. Org. Chem. 2002, 67, 3718-3723; D. A. Evans, J. L. Katz, G. S. Peterson, T. Hintermann, J. Am. Chem. Soc. 2001, 123, 12411-12413; C. P. Decicco, Y. Song, D. A. Evans, Org. Lett. 2001, 3, 1029-1032; J. C. Antilla, S. L. Buchwald, Org. Lett. 2001, 3, 2077-2079; T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2000, 611, 392-402, and references therein; M. Murata, T. Oyama, S. Watanabe, Y. Masuda, J. Org. Chem. 2000, 65, 164-168.
37. R. B. Bedford, C. S. J. Cazin, S. J. Coles, T. Gelbrich, P. N. Horton, M. B. Hursthouse, M. E. Light, Organometallics 2003, 22, 987-999; N. R. Anastasi, K. M. Waltz, W. L. Weerakoon, J. F. Hartwig, Organometallics 2003, 22, 365-369, and references therein; D. E. Portlock, R. Ostaszewski, D. Naskar, L. West, Tetrahedron Lett. 2003, 44, 603-605; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691-1694, and references therein; G. W. Kabalka, S. K. Guchhait, Org. Lett. 2003, 5, 729-731; G. W. Kabalka, B. Venkataiah, Tetrahedron Lett. 2002, 43, 3703-3705; G. K. S. Prakash, M. Mandal, S. Schweizer, N. A. Petasis, G. A. Olah, J. Org. Chem. 2002, 67, 3718-3723; D. A. Evans, J. L. Katz, G. S. Peterson, T. Hintermann, J. Am. Chem. Soc. 2001, 123, 12411-12413; C. P. Decicco, Y. Song, D. A. Evans, Org. Lett. 2001, 3, 1029-1032; J. C. Antilla, S. L. Buchwald, Org. Lett. 2001, 3, 2077-2079; T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2000, 611, 392-402, and references therein; M. Murata, T. Oyama, S. Watanabe, Y. Masuda, J. Org. Chem. 2000, 65, 164-168.
38. R. B. Bedford, C. S. J. Cazin, S. J. Coles, T. Gelbrich, P. N. Horton, M. B. Hursthouse, M. E. Light, Organometallics 2003, 22, 987-999; N. R. Anastasi, K. M. Waltz, W. L. Weerakoon, J. F. Hartwig, Organometallics 2003, 22, 365-369, and references therein; D. E. Portlock, R. Ostaszewski, D. Naskar, L. West, Tetrahedron Lett. 2003, 44, 603-605; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691-1694, and references therein; G. W. Kabalka, S. K. Guchhait, Org. Lett. 2003, 5, 729-731; G. W. Kabalka, B. Venkataiah, Tetrahedron Lett. 2002, 43, 3703-3705; G. K. S. Prakash, M. Mandal, S. Schweizer, N. A. Petasis, G. A. Olah, J. Org. Chem. 2002, 67, 3718-3723; D. A. Evans, J. L. Katz, G. S. Peterson, T. Hintermann, J. Am. Chem. Soc. 2001, 123, 12411-12413; C. P. Decicco, Y. Song, D. A. Evans, Org. Lett. 2001, 3, 1029-1032; J. C. Antilla, S. L. Buchwald, Org. Lett. 2001, 3, 2077-2079; T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2000, 611, 392-402, and references therein; M. Murata, T. Oyama, S. Watanabe, Y. Masuda, J. Org. Chem. 2000, 65, 164-168.
39. R. B. Bedford, C. S. J. Cazin, S. J. Coles, T. Gelbrich, P. N. Horton, M. B. Hursthouse, M. E. Light, Organometallics 2003, 22, 987-999; N. R. Anastasi, K. M. Waltz, W. L. Weerakoon, J. F. Hartwig, Organometallics 2003, 22, 365-369, and references therein; D. E. Portlock, R. Ostaszewski, D. Naskar, L. West, Tetrahedron Lett. 2003, 44, 603-605; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691-1694, and references therein; G. W. Kabalka, S. K. Guchhait, Org. Lett. 2003, 5, 729-731; G. W. Kabalka, B. Venkataiah, Tetrahedron Lett. 2002, 43, 3703-3705; G. K. S. Prakash, M. Mandal, S. Schweizer, N. A. Petasis, G. A. Olah, J. Org. Chem. 2002, 67, 3718-3723; D. A. Evans, J. L. Katz, G. S. Peterson, T. Hintermann, J. Am. Chem. Soc. 2001, 123, 12411-12413; C. P. Decicco, Y. Song, D. A. Evans, Org. Lett. 2001, 3, 1029-1032; J. C. Antilla, S. L. Buchwald, Org. Lett. 2001, 3, 2077-2079; T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2000, 611, 392-402, and references therein; M. Murata, T. Oyama, S. Watanabe, Y. Masuda, J. Org. Chem. 2000, 65, 164-168.
40. R. B. Bedford, C. S. J. Cazin, S. J. Coles, T. Gelbrich, P. N. Horton, M. B. Hursthouse, M. E. Light, Organometallics 2003, 22, 987-999; N. R. Anastasi, K. M. Waltz, W. L. Weerakoon, J. F. Hartwig, Organometallics 2003, 22, 365-369, and references therein; D. E. Portlock, R. Ostaszewski, D. Naskar, L. West, Tetrahedron Lett. 2003, 44, 603-605; P. Y. S. Lam, D. Bonne, G. Vincent, C. G. Clark, A. P. Combs, Tetrahedron Lett. 2003, 44, 1691-1694, and references therein; G. W. Kabalka, S. K. Guchhait, Org. Lett. 2003, 5, 729-731; G. W. Kabalka, B. Venkataiah, Tetrahedron Lett. 2002, 43, 3703-3705; G. K. S. Prakash, M. Mandal, S. Schweizer, N. A. Petasis, G. A. Olah, J. Org. Chem. 2002, 67, 3718-3723; D. A. Evans, J. L. Katz, G. S. Peterson, T. Hintermann, J. Am. Chem. Soc. 2001, 123, 12411-12413; C. P. Decicco, Y. Song, D. A. Evans, Org. Lett. 2001, 3, 1029-1032; J. C. Antilla, S. L. Buchwald, Org. Lett. 2001, 3, 2077-2079; T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2000, 611, 392-402, and references therein; M. Murata, T. Oyama, S. Watanabe, Y. Masuda, J. Org. Chem. 2000, 65, 164-168.
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62. J.-G. Boiteau, R. Imbos, A. J. Minnaard, B. L. Feringa, Org. Lett. 2003, 5, 681-684; D. F. Cauble, J. D. Gipson, M. J. Krische, J. Am. Chem. Soc. 2003, 125, 1110-1111; C. Bolm, J. Rudolph, J. Am. Chem. Soc. 2002, 124, 14850-14851; K. Yoshida, M. Ogasawara, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 10984-10985; T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 2002, 124, 5052-5058; M. Kuriyama, K. Nagai, K.-i. Yamada, Y. Miwa, T. Taga, K. Tomioka, J. Am. Chem. Soc. 2002, 124, 8932-8939; M. Pucheault, S. Darses, J.-P. Genet, Eur. J. Org. Chem. 2002, 3552-3557; M. Lautens, C. Dockendorff, K. Fagnou, A. Malicki, Org. Lett. 2002, 4, 1311-1314; for recent reviews, see: G. Alvaro, D. Savoia, Synlett 2002, 651-673; A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221-3226; N. Krause, Hoffmann-Röder, Synthesis 2001, 171-196; T. Hayashi, Synlett 2001, 879-887; M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061; S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069-1094; R. Bloch, Chem. Rev. 1998, 98, 1407-1438; D. Enders, U. Reinhold, Tetrahedron: Asymmetry 1997, 8, 1895-1946.
63. J.-G. Boiteau, R. Imbos, A. J. Minnaard, B. L. Feringa, Org. Lett. 2003, 5, 681-684; D. F. Cauble, J. D. Gipson, M. J. Krische, J. Am. Chem. Soc. 2003, 125, 1110-1111; C. Bolm, J. Rudolph, J. Am. Chem. Soc. 2002, 124, 14850-14851; K. Yoshida, M. Ogasawara, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 10984-10985; T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 2002, 124, 5052-5058; M. Kuriyama, K. Nagai, K.-i. Yamada, Y. Miwa, T. Taga, K. Tomioka, J. Am. Chem. Soc. 2002, 124, 8932-8939; M. Pucheault, S. Darses, J.-P. Genet, Eur. J. Org. Chem. 2002, 3552-3557; M. Lautens, C. Dockendorff, K. Fagnou, A. Malicki, Org. Lett. 2002, 4, 1311-1314; for recent reviews, see: G. Alvaro, D. Savoia, Synlett 2002, 651-673; A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221-3226; N. Krause, Hoffmann-Röder, Synthesis 2001, 171-196; T. Hayashi, Synlett 2001, 879-887; M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061; S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069-1094; R. Bloch, Chem. Rev. 1998, 98, 1407-1438; D. Enders, U. Reinhold, Tetrahedron: Asymmetry 1997, 8, 1895-1946.
64. J.-G. Boiteau, R. Imbos, A. J. Minnaard, B. L. Feringa, Org. Lett. 2003, 5, 681-684; D. F. Cauble, J. D. Gipson, M. J. Krische, J. Am. Chem. Soc. 2003, 125, 1110-1111; C. Bolm, J. Rudolph, J. Am. Chem. Soc. 2002, 124, 14850-14851; K. Yoshida, M. Ogasawara, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 10984-10985; T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 2002, 124, 5052-5058; M. Kuriyama, K. Nagai, K.-i. Yamada, Y. Miwa, T. Taga, K. Tomioka, J. Am. Chem. Soc. 2002, 124, 8932-8939; M. Pucheault, S. Darses, J.-P. Genet, Eur. J. Org. Chem. 2002, 3552-3557; M. Lautens, C. Dockendorff, K. Fagnou, A. Malicki, Org. Lett. 2002, 4, 1311-1314; for recent reviews, see: G. Alvaro, D. Savoia, Synlett 2002, 651-673; A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221-3226; N. Krause, Hoffmann-Röder, Synthesis 2001, 171-196; T. Hayashi, Synlett 2001, 879-887; M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061; S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069-1094; R. Bloch, Chem. Rev. 1998, 98, 1407-1438; D. Enders, U. Reinhold, Tetrahedron: Asymmetry 1997, 8, 1895-1946.
65. J.-G. Boiteau, R. Imbos, A. J. Minnaard, B. L. Feringa, Org. Lett. 2003, 5, 681-684; D. F. Cauble, J. D. Gipson, M. J. Krische, J. Am. Chem. Soc. 2003, 125, 1110-1111; C. Bolm, J. Rudolph, J. Am. Chem. Soc. 2002, 124, 14850-14851; K. Yoshida, M. Ogasawara, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 10984-10985; T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 2002, 124, 5052-5058; M. Kuriyama, K. Nagai, K.-i. Yamada, Y. Miwa, T. Taga, K. Tomioka, J. Am. Chem. Soc. 2002, 124, 8932-8939; M. Pucheault, S. Darses, J.-P. Genet, Eur. J. Org. Chem. 2002, 3552-3557; M. Lautens, C. Dockendorff, K. Fagnou, A. Malicki, Org. Lett. 2002, 4, 1311-1314; for recent reviews, see: G. Alvaro, D. Savoia, Synlett 2002, 651-673; A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221-3226; N. Krause, Hoffmann-Röder, Synthesis 2001, 171-196; T. Hayashi, Synlett 2001, 879-887; M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061; S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069-1094; R. Bloch, Chem. Rev. 1998, 98, 1407-1438; D. Enders, U. Reinhold, Tetrahedron: Asymmetry 1997, 8, 1895-1946.
66. J.-G. Boiteau, R. Imbos, A. J. Minnaard, B. L. Feringa, Org. Lett. 2003, 5, 681-684; D. F. Cauble, J. D. Gipson, M. J. Krische, J. Am. Chem. Soc. 2003, 125, 1110-1111; C. Bolm, J. Rudolph, J. Am. Chem. Soc. 2002, 124, 14850-14851; K. Yoshida, M. Ogasawara, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 10984-10985; T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 2002, 124, 5052-5058; M. Kuriyama, K. Nagai, K.-i. Yamada, Y. Miwa, T. Taga, K. Tomioka, J. Am. Chem. Soc. 2002, 124, 8932-8939; M. Pucheault, S. Darses, J.-P. Genet, Eur. J. Org. Chem. 2002, 3552-3557; M. Lautens, C. Dockendorff, K. Fagnou, A. Malicki, Org. Lett. 2002, 4, 1311-1314; for recent reviews, see: G. Alvaro, D. Savoia, Synlett 2002, 651-673; A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221-3226; N. Krause, Hoffmann-Röder, Synthesis 2001, 171-196; T. Hayashi, Synlett 2001, 879-887; M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061; S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069-1094; R. Bloch, Chem. Rev. 1998, 98, 1407-1438; D. Enders, U. Reinhold, Tetrahedron: Asymmetry 1997, 8, 1895-1946.
67. J.-G. Boiteau, R. Imbos, A. J. Minnaard, B. L. Feringa, Org. Lett. 2003, 5, 681-684; D. F. Cauble, J. D. Gipson, M. J. Krische, J. Am. Chem. Soc. 2003, 125, 1110-1111; C. Bolm, J. Rudolph, J. Am. Chem. Soc. 2002, 124, 14850-14851; K. Yoshida, M. Ogasawara, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 10984-10985; T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 2002, 124, 5052-5058; M. Kuriyama, K. Nagai, K.-i. Yamada, Y. Miwa, T. Taga, K. Tomioka, J. Am. Chem. Soc. 2002, 124, 8932-8939; M. Pucheault, S. Darses, J.-P. Genet, Eur. J. Org. Chem. 2002, 3552-3557; M. Lautens, C. Dockendorff, K. Fagnou, A. Malicki, Org. Lett. 2002, 4, 1311-1314; for recent reviews, see: G. Alvaro, D. Savoia, Synlett 2002, 651-673; A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221-3226; N. Krause, Hoffmann-Röder, Synthesis 2001, 171-196; T. Hayashi, Synlett 2001, 879-887; M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061; S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069-1094; R. Bloch, Chem. Rev. 1998, 98, 1407-1438; D. Enders, U. Reinhold, Tetrahedron: Asymmetry 1997, 8, 1895-1946.
68. J.-G. Boiteau, R. Imbos, A. J. Minnaard, B. L. Feringa, Org. Lett. 2003, 5, 681-684; D. F. Cauble, J. D. Gipson, M. J. Krische, J. Am. Chem. Soc. 2003, 125, 1110-1111; C. Bolm, J. Rudolph, J. Am. Chem. Soc. 2002, 124, 14850-14851; K. Yoshida, M. Ogasawara, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 10984-10985; T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 2002, 124, 5052-5058; M. Kuriyama, K. Nagai, K.-i. Yamada, Y. Miwa, T. Taga, K. Tomioka, J. Am. Chem. Soc. 2002, 124, 8932-8939; M. Pucheault, S. Darses, J.-P. Genet, Eur. J. Org. Chem. 2002, 3552-3557; M. Lautens, C. Dockendorff, K. Fagnou, A. Malicki, Org. Lett. 2002, 4, 1311-1314; for recent reviews, see: G. Alvaro, D. Savoia, Synlett 2002, 651-673; A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221-3226; N. Krause, Hoffmann-Röder, Synthesis 2001, 171-196; T. Hayashi, Synlett 2001, 879-887; M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061; S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069-1094; R. Bloch, Chem. Rev. 1998, 98, 1407-1438; D. Enders, U. Reinhold, Tetrahedron: Asymmetry 1997, 8, 1895-1946.
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71. J.-G. Boiteau, R. Imbos, A. J. Minnaard, B. L. Feringa, Org. Lett. 2003, 5, 681-684; D. F. Cauble, J. D. Gipson, M. J. Krische, J. Am. Chem. Soc. 2003, 125, 1110-1111; C. Bolm, J. Rudolph, J. Am. Chem. Soc. 2002, 124, 14850-14851; K. Yoshida, M. Ogasawara, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 10984-10985; T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 2002, 124, 5052-5058; M. Kuriyama, K. Nagai, K.-i. Yamada, Y. Miwa, T. Taga, K. Tomioka, J. Am. Chem. Soc. 2002, 124, 8932-8939; M. Pucheault, S. Darses, J.-P. Genet, Eur. J. Org. Chem. 2002, 3552-3557; M. Lautens, C. Dockendorff, K. Fagnou, A. Malicki, Org. Lett. 2002, 4, 1311-1314; for recent reviews, see: G. Alvaro, D. Savoia, Synlett 2002, 651-673; A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221-3226; N. Krause, Hoffmann-Röder, Synthesis 2001, 171-196; T. Hayashi, Synlett 2001, 879-887; M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061; S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069-1094; R. Bloch, Chem. Rev. 1998, 98, 1407-1438; D. Enders, U. Reinhold, Tetrahedron: Asymmetry 1997, 8, 1895-1946.
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78. B. M. Mikhailov, A. Ya. Bezmenov, L. S. Vasil'ev, V. G. Kiselev, Dokl. Akad. Nauk SSSR 1964, 155, 141; A. Ya. Bezmenov, L. S. Vasil'ev, B. M. Mikhailov, Izv. Akad. Nauk SSSR Ser. Khim. 1965, 2111; B. M. Mikhailov, Organomet. Chem. Rev. Sect. A 1972, 8, 1-65.
79. B. M. Mikhailov, A. Ya. Bezmenov, L. S. Vasil'ev, V. G. Kiselev, Dokl. Akad. Nauk SSSR 1964, 155, 141; A. Ya. Bezmenov, L. S. Vasil'ev, B. M. Mikhailov, Izv. Akad. Nauk SSSR Ser. Khim. 1965, 2111; B. M. Mikhailov, Organomet. Chem. Rev. Sect. A 1972, 8, 1-65.
80. B. M. Mikhailov, A. Ya. Bezmenov, L. S. Vasil'ev, V. G. Kiselev, Dokl. Akad. Nauk SSSR 1964, 155, 141; A. Ya. Bezmenov, L. S. Vasil'ev, B. M. Mikhailov, Izv. Akad. Nauk SSSR Ser. Khim. 1965, 2111; B. M. Mikhailov, Organomet. Chem. Rev. Sect. A 1972, 8, 1-65.
81. H. C. Brown, R. Liotta, G. W. Kramer, J. Org. Chem. 1978, 43, 1058-1063; also see M. Zaidlewicz, J. Meller, Tetrahedron Lett. 1997, 38, 7279-7282.
82. H. C. Brown, R. Liotta, G. W. Kramer, J. Org. Chem. 1978, 43, 1058-1063; also see M. Zaidlewicz, J. Meller, Tetrahedron Lett. 1997, 38, 7279-7282.
83. H. C. Brown, G. Zweifel, J. Am. Chem. Soc. 1961, 83, 3834-3840; G. Zweifel, G. M. Clark, N. L. Polston, J. Am. Chem. Soc. 1971, 93, 3395-3399; H. C. Brown, G. Zweifel, J. Am. Chem. Soc. 1961, 83, 1241-1246; J. A. Soderquist, A. Hassner, J. Organomet. Chem. 1978, 156, C12-C16; H. C. Brown, J. Chen, J. Org. Chem. 1981, 46, 3978-3988; Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 2295-2298.
84. H. C. Brown, G. Zweifel, J. Am. Chem. Soc. 1961, 83, 3834-3840; G. Zweifel, G. M. Clark, N. L. Polston, J. Am. Chem. Soc. 1971, 93, 3395-3399; H. C. Brown, G. Zweifel, J. Am. Chem. Soc. 1961, 83, 1241-1246; J. A. Soderquist, A. Hassner, J. Organomet. Chem. 1978, 156, C12-C16; H. C. Brown, J. Chen, J. Org. Chem. 1981, 46, 3978-3988; Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 2295-2298.
85. H. C. Brown, G. Zweifel, J. Am. Chem. Soc. 1961, 83, 3834-3840; G. Zweifel, G. M. Clark, N. L. Polston, J. Am. Chem. Soc. 1971, 93, 3395-3399; H. C. Brown, G. Zweifel, J. Am. Chem. Soc. 1961, 83, 1241-1246; J. A. Soderquist, A. Hassner, J. Organomet. Chem. 1978, 156, C12-C16; H. C. Brown, J. Chen, J. Org. Chem. 1981, 46, 3978-3988; Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 2295-2298.
86. H. C. Brown, G. Zweifel, J. Am. Chem. Soc. 1961, 83, 3834-3840; G. Zweifel, G. M. Clark, N. L. Polston, J. Am. Chem. Soc. 1971, 93, 3395-3399; H. C. Brown, G. Zweifel, J. Am. Chem. Soc. 1961, 83, 1241-1246; J. A. Soderquist, A. Hassner, J. Organomet. Chem. 1978, 156, C12-C16; H. C. Brown, J. Chen, J. Org. Chem. 1981, 46, 3978-3988; Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 2295-2298.
87. H. C. Brown, G. Zweifel, J. Am. Chem. Soc. 1961, 83, 3834-3840; G. Zweifel, G. M. Clark, N. L. Polston, J. Am. Chem. Soc. 1971, 93, 3395-3399; H. C. Brown, G. Zweifel, J. Am. Chem. Soc. 1961, 83, 1241-1246; J. A. Soderquist, A. Hassner, J. Organomet. Chem. 1978, 156, C12-C16; H. C. Brown, J. Chen, J. Org. Chem. 1981, 46, 3978-3988; Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 2295-2298.
88. H. C. Brown, G. Zweifel, J. Am. Chem. Soc. 1961, 83, 3834-3840; G. Zweifel, G. M. Clark, N. L. Polston, J. Am. Chem. Soc. 1971, 93, 3395-3399; H. C. Brown, G. Zweifel, J. Am. Chem. Soc. 1961, 83, 1241-1246; J. A. Soderquist, A. Hassner, J. Organomet. Chem. 1978, 156, C12-C16; H. C. Brown, J. Chen, J. Org. Chem. 1981, 46, 3978-3988; Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 2295-2298.
89. B. M. Mikhailov, Yu. N. Bubnov, Izv. Akad. Nauk SSSR Ser. Khim. 1964, 1874; P. Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207-2293; R. Hoffmann, J. Krüger, D. Brückner, New J. Chem. 2001, 25, 102-107; J. W. J. Kennedy, D. G. Hall, J. Am. Chem. Soc. 2002, 124, 898-899; Y. Yamamoto, M. Takahashi, N. Miyaura, Synlett 2002, 128-130; M. C. Kozlowski, S. P. Waters, J. W. Skudlarek, C. A. Evans, Org. Lett. 2002, 4, 4391-4393; Y. Yamamoto, K. Kurihara, A. Yamada, M. Takahashi, Y. Takahashi, N. Miyaura, Tetrahedron 2003, 59, 537-542.
90. B. M. Mikhailov, Yu. N. Bubnov, Izv. Akad. Nauk SSSR Ser. Khim. 1964, 1874; P. Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207-2293; R. Hoffmann, J. Krüger, D. Brückner, New J. Chem. 2001, 25, 102-107; J. W. J. Kennedy, D. G. Hall, J. Am. Chem. Soc. 2002, 124, 898-899; Y. Yamamoto, M. Takahashi, N. Miyaura, Synlett 2002, 128-130; M. C. Kozlowski, S. P. Waters, J. W. Skudlarek, C. A. Evans, Org. Lett. 2002, 4, 4391-4393; Y. Yamamoto, K. Kurihara, A. Yamada, M. Takahashi, Y. Takahashi, N. Miyaura, Tetrahedron 2003, 59, 537-542.
91. B. M. Mikhailov, Yu. N. Bubnov, Izv. Akad. Nauk SSSR Ser. Khim. 1964, 1874; P. Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207-2293; R. Hoffmann, J. Krüger, D. Brückner, New J. Chem. 2001, 25, 102-107; J. W. J. Kennedy, D. G. Hall, J. Am. Chem. Soc. 2002, 124, 898-899; Y. Yamamoto, M. Takahashi, N. Miyaura, Synlett 2002, 128-130; M. C. Kozlowski, S. P. Waters, J. W. Skudlarek, C. A. Evans, Org. Lett. 2002, 4, 4391-4393; Y. Yamamoto, K. Kurihara, A. Yamada, M. Takahashi, Y. Takahashi, N. Miyaura, Tetrahedron 2003, 59, 537-542.
92. B. M. Mikhailov, Yu. N. Bubnov, Izv. Akad. Nauk SSSR Ser. Khim. 1964, 1874; P. Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207-2293; R. Hoffmann, J. Krüger, D. Brückner, New J. Chem. 2001, 25, 102-107; J. W. J. Kennedy, D. G. Hall, J. Am. Chem. Soc. 2002, 124, 898-899; Y. Yamamoto, M. Takahashi, N. Miyaura, Synlett 2002, 128-130; M. C. Kozlowski, S. P. Waters, J. W. Skudlarek, C. A. Evans, Org. Lett. 2002, 4, 4391-4393; Y. Yamamoto, K. Kurihara, A. Yamada, M. Takahashi, Y. Takahashi, N. Miyaura, Tetrahedron 2003, 59, 537-542.
93. B. M. Mikhailov, Yu. N. Bubnov, Izv. Akad. Nauk SSSR Ser. Khim. 1964, 1874; P. Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207-2293; R. Hoffmann, J. Krüger, D. Brückner, New J. Chem. 2001, 25, 102-107; J. W. J. Kennedy, D. G. Hall, J. Am. Chem. Soc. 2002, 124, 898-899; Y. Yamamoto, M. Takahashi, N. Miyaura, Synlett 2002, 128-130; M. C. Kozlowski, S. P. Waters, J. W. Skudlarek, C. A. Evans, Org. Lett. 2002, 4, 4391-4393; Y. Yamamoto, K. Kurihara, A. Yamada, M. Takahashi, Y. Takahashi, N. Miyaura, Tetrahedron 2003, 59, 537-542.
94. B. M. Mikhailov, Yu. N. Bubnov, Izv. Akad. Nauk SSSR Ser. Khim. 1964, 1874; P. Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207-2293; R. Hoffmann, J. Krüger, D. Brückner, New J. Chem. 2001, 25, 102-107; J. W. J. Kennedy, D. G. Hall, J. Am. Chem. Soc. 2002, 124, 898-899; Y. Yamamoto, M. Takahashi, N. Miyaura, Synlett 2002, 128-130; M. C. Kozlowski, S. P. Waters, J. W. Skudlarek, C. A. Evans, Org. Lett. 2002, 4, 4391-4393; Y. Yamamoto, K. Kurihara, A. Yamada, M. Takahashi, Y. Takahashi, N. Miyaura, Tetrahedron 2003, 59, 537-542.
95. B. M. Mikhailov, Yu. N. Bubnov, Izv. Akad. Nauk SSSR Ser. Khim. 1964, 1874; P. Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207-2293; R. Hoffmann, J. Krüger, D. Brückner, New J. Chem. 2001, 25, 102-107; J. W. J. Kennedy, D. G. Hall, J. Am. Chem. Soc. 2002, 124, 898-899; Y. Yamamoto, M. Takahashi, N. Miyaura, Synlett 2002, 128-130; M. C. Kozlowski, S. P. Waters, J. W. Skudlarek, C. A. Evans, Org. Lett. 2002, 4, 4391-4393; Y. Yamamoto, K. Kurihara, A. Yamada, M. Takahashi, Y. Takahashi, N. Miyaura, Tetrahedron 2003, 59, 537-542.
96. The ease of hydrolysis of simple allyl boranes diminishes with increasing substitution of double bond: triallylborane reacts rapidly with alcohols at room temperature with formation of allylboronic anhydride after distillation under vacuum: B. M. Mikhailov, F. B. Tutorskaya, Dokl. Akad. Nauk SSSR 1958, 479; tricrotylborane reacts with methanol at room temperature to give dicrotylmethoxyborane (hydrolysis of only one organic residue on the boron center); to cleave the second crotyl residue, heating in methanol is required: B. M. Mikhailov, V. F. Pozdnev, Izv. Akad. Nauk SSSR Ser. Khim. 1964, 1477.
97. The ease of hydrolysis of simple allyl boranes diminishes with increasing substitution of double bond: triallylborane reacts rapidly with alcohols at room temperature with formation of allylboronic anhydride after distillation under vacuum: B. M. Mikhailov, F. B. Tutorskaya, Dokl. Akad. Nauk SSSR 1958, 479; tricrotylborane reacts with methanol at room temperature to give dicrotylmethoxyborane (hydrolysis of only one organic residue on the boron center); to cleave the second crotyl residue, heating in methanol is required: B. M. Mikhailov, V. F. Pozdnev, Izv. Akad. Nauk SSSR Ser. Khim. 1964, 1477.
98. H. C. Brown, S. K. Gupta, J. Am. Chem. Soc. 1975, 97, 5249-5255; Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 1017-1020.
99. H. C. Brown, S. K. Gupta, J. Am. Chem. Soc. 1975, 97, 5249-5255; Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 1017-1020.
100. H. C. Brown, N. G. Bhat, V. Somayaji, Organometallics 1983, 2, 1311-1316; H. C. Brown, U. S. Racherla, J. Org. Chem. 1986, 51, 895-897; H. C. Brown, J. B. Campbell, Jr., J. Org. Chem. 1980, 45, 389-395; Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 1548-1552 and 1689-1690.
101. H. C. Brown, N. G. Bhat, V. Somayaji, Organometallics 1983, 2, 1311-1316; H. C. Brown, U. S. Racherla, J. Org. Chem. 1986, 51, 895-897; H. C. Brown, J. B. Campbell, Jr., J. Org. Chem. 1980, 45, 389-395; Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 1548-1552 and 1689-1690.
102. H. C. Brown, N. G. Bhat, V. Somayaji, Organometallics 1983, 2, 1311-1316; H. C. Brown, U. S. Racherla, J. Org. Chem. 1986, 51, 895-897; H. C. Brown, J. B. Campbell, Jr., J. Org. Chem. 1980, 45, 389-395; Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 1548-1552 and 1689-1690.
103. H. C. Brown, N. G. Bhat, V. Somayaji, Organometallics 1983, 2, 1311-1316; H. C. Brown, U. S. Racherla, J. Org. Chem. 1986, 51, 895-897; H. C. Brown, J. B. Campbell, Jr., J. Org. Chem. 1980, 45, 389-395; Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 1548-1552 and 1689-1690.
104. R. Köster in Methods of Organic Chemistry (Houben-Weyl), 4th ed. 1952-, Vol. 13/3a, 1982, pp. 489-853.
105. The well-documented reduction of halides, sulfonates, and sulfates with sodium borohydride proceeds well in polar aprotic solvents such as diglyme or dimethyl sulfoxide with the generation of an equimolar amount of borane. This consideration led to the development of protocols with borane being scavenged in situ by the present alkene, thus resulting in a hydroboration reaction in situ: H. C. Brown, P. Tierney, J. Am. Chem. Soc. 1958, 80, 1552-1558; H. C. Brown, K. J. Murray, L. J. Murray, J. A. Snover, G. Zweifel, J. Am. Chem. Soc. 1960, 82, 4233-4241; H. M. Bell, C. W. Vanderslice, A. Spehar, J. Org. Chem. 1969, 34, 3923-3926; S. Krishnamurthy, H. C. Brown, J. Org. Chem. 1980, 45, 849-856; Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 4522-4528.
106. The well-documented reduction of halides, sulfonates, and sulfates with sodium borohydride proceeds well in polar aprotic solvents such as diglyme or dimethyl sulfoxide with the generation of an equimolar amount of borane. This consideration led to the development of protocols with borane being scavenged in situ by the present alkene, thus resulting in a hydroboration reaction in situ: H. C. Brown, P. Tierney, J. Am. Chem. Soc. 1958, 80, 1552-1558; H. C. Brown, K. J. Murray, L. J. Murray, J. A. Snover, G. Zweifel, J. Am. Chem. Soc. 1960, 82, 4233-4241; H. M. Bell, C. W. Vanderslice, A. Spehar, J. Org. Chem. 1969, 34, 3923-3926; S. Krishnamurthy, H. C. Brown, J. Org. Chem. 1980, 45, 849-856; Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 4522-4528.
107. The well-documented reduction of halides, sulfonates, and sulfates with sodium borohydride proceeds well in polar aprotic solvents such as diglyme or dimethyl sulfoxide with the generation of an equimolar amount of borane. This consideration led to the development of protocols with borane being scavenged in situ by the present alkene, thus resulting in a hydroboration reaction in situ: H. C. Brown, P. Tierney, J. Am. Chem. Soc. 1958, 80, 1552-1558; H. C. Brown, K. J. Murray, L. J. Murray, J. A. Snover, G. Zweifel, J. Am. Chem. Soc. 1960, 82, 4233-4241; H. M. Bell, C. W. Vanderslice, A. Spehar, J. Org. Chem. 1969, 34, 3923-3926; S. Krishnamurthy, H. C. Brown, J. Org. Chem. 1980, 45, 849-856; Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 4522-4528.
108. The well-documented reduction of halides, sulfonates, and sulfates with sodium borohydride proceeds well in polar aprotic solvents such as diglyme or dimethyl sulfoxide with the generation of an equimolar amount of borane. This consideration led to the development of protocols with borane being scavenged in situ by the present alkene, thus resulting in a hydroboration reaction in situ: H. C. Brown, P. Tierney, J. Am. Chem. Soc. 1958, 80, 1552-1558; H. C. Brown, K. J. Murray, L. J. Murray, J. A. Snover, G. Zweifel, J. Am. Chem. Soc. 1960, 82, 4233-4241; H. M. Bell, C. W. Vanderslice, A. Spehar, J. Org. Chem. 1969, 34, 3923-3926; S. Krishnamurthy, H. C. Brown, J. Org. Chem. 1980, 45, 849-856; Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 4522-4528.
109. The well-documented reduction of halides, sulfonates, and sulfates with sodium borohydride proceeds well in polar aprotic solvents such as diglyme or dimethyl sulfoxide with the generation of an equimolar amount of borane. This consideration led to the development of protocols with borane being scavenged in situ by the present alkene, thus resulting in a hydroboration reaction in situ: H. C. Brown, P. Tierney, J. Am. Chem. Soc. 1958, 80, 1552-1558; H. C. Brown, K. J. Murray, L. J. Murray, J. A. Snover, G. Zweifel, J. Am. Chem. Soc. 1960, 82, 4233-4241; H. M. Bell, C. W. Vanderslice, A. Spehar, J. Org. Chem. 1969, 34, 3923-3926; S. Krishnamurthy, H. C. Brown, J. Org. Chem. 1980, 45, 849-856; Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 4522-4528.
110. Unlike boronic acids, the corresponding diethanolamine adducts are highly stable, conveniently handled and purified compounds: K. Smith, J. B. Leach, Organometallic Compounds of Boron, Chapman and Hall, New York, 1985; see also: M. Gravel, K. A. Thompson, M. Zak, C. Berube, D. G. Hall, J. Org. Chem. 2002, 67, 3-15; C. N. Farthing, S. P. Marsden, Tetrahedron Lett. 2000, 41, 4235-4238; K. A. Thompson, D. G. Hall, Chem. Commun. 2000, 2379-2380.
111. Unlike boronic acids, the corresponding diethanolamine adducts are highly stable, conveniently handled and purified compounds: K. Smith, J. B. Leach, Organometallic Compounds of Boron, Chapman and Hall, New York, 1985; see also: M. Gravel, K. A. Thompson, M. Zak, C. Berube, D. G. Hall, J. Org. Chem. 2002, 67, 3-15; C. N. Farthing, S. P. Marsden, Tetrahedron Lett. 2000, 41, 4235-4238; K. A. Thompson, D. G. Hall, Chem. Commun. 2000, 2379-2380.
112. Unlike boronic acids, the corresponding diethanolamine adducts are highly stable, conveniently handled and purified compounds: K. Smith, J. B. Leach, Organometallic Compounds of Boron, Chapman and Hall, New York, 1985; see also: M. Gravel, K. A. Thompson, M. Zak, C. Berube, D. G. Hall, J. Org. Chem. 2002, 67, 3-15; C. N. Farthing, S. P. Marsden, Tetrahedron Lett. 2000, 41, 4235-4238; K. A. Thompson, D. G. Hall, Chem. Commun. 2000, 2379-2380.
113. Unlike boronic acids, the corresponding diethanolamine adducts are highly stable, conveniently handled and purified compounds: K. Smith, J. B. Leach, Organometallic Compounds of Boron, Chapman and Hall, New York, 1985; see also: M. Gravel, K. A. Thompson, M. Zak, C. Berube, D. G. Hall, J. Org. Chem. 2002, 67, 3-15; C. N. Farthing, S. P. Marsden, Tetrahedron Lett. 2000, 41, 4235-4238; K. A. Thompson, D. G. Hall, Chem. Commun. 2000, 2379-2380.
114. For experimental details, see Supporting Information.
115. Experiments to isolate 9 were not conducted (see reference [17]).
116. CCDC 193 654 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ ccdc.cam.ac.uk).
117. E. Jehanno, M. Vaultier, Tetrahedron Lett. 1995, 36, 4439-4442; J. Tailor, D. G. Hall, Org. Lett. 2000, 2, 3715-3718.
118. E. Jehanno, M. Vaultier, Tetrahedron Lett. 1995, 36, 4439-4442; J. Tailor, D. G. Hall, Org. Lett. 2000, 2, 3715-3718.