A highly practical and enantioselective reagent for the allylation of aldehydes

Angewandte Chemie - International Edition

Volumn 42, Issue 8, 2003, Pages 946-948

  Kubota, Katsumi ^a   Leighton, James L ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

Aldehydes; Allylation; Asymmetric synthesis; Chiral auxiliaries; Homoallylic alcohols

Indexed keywords

DECOMPOSITION; SILICON;

ALLYLATION; ENANTIOSELECTIVE REAGENT;

ALDEHYDES;

ALDEHYDE; CYCLOPENTANE DERIVATIVE; LEWIS ACID; REAGENT; SILICON;

ALLYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; DECOMPOSITION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REACTION OPTIMIZATION; TEMPERATURE DEPENDENCE;

EID: 0037463065     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390252     Document Type: Article

References (28)

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17. For a recent review of enantioselective Lewis acid catalyzed allylmetal additions, see: a) A. Yanagisawa in Comprehensive Asymmetric Catalysis, Vol. II (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 1999, chap. 27. Enantioselective Lewis base catalysis: b) S. E. Denmark, D. M. Coe, N. E. Pratt, B. D. Griedel, J. Org. Chem. 1994, 59, 6161; c) S. E. Denmark, J. Fu, J. Am. Chem. Soc. 2000, 122, 12021; d) S. E. Denmark, J. Fu, J. Am. Chem. Soc. 2001, 123, 9488; e) K. Iseki, Y. Kuroki, M. Takahashi, Y. Kobayashi, Tetrahedron Lett. 1996, 37, 5149; f) K. Iseki, Y. Kuroki, M. Takahashi, S. Kishimoto, Y. Kobayashi, Tetrahedron 1997, 53, 3513; g) K. Iseki, S. Mizuno, Y. Kuroki, Y. Kobayashi, Tetrahedron Lett. 1998, 39, 2767; h) K. Iseki, S. Mizuno, Y. Kuroki, Y. Kobayashi, Tetrahedron 1999, 55, 977; i) M. Nakajima, M. Saito, M. Shiro, S. Hashimoto, J. Am. Chem. Soc. 1998, 120, 6419; j) A. V. Malkov, M. Orsini, D. Pernazza, K. W. Muir, V. Langer, P. Meghani, P. Kocovsky, Org. Lett. 2002, 4, 1047.
18. For a recent review of enantioselective Lewis acid catalyzed allylmetal additions, see: a) A. Yanagisawa in Comprehensive Asymmetric Catalysis, Vol. II (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 1999, chap. 27. Enantioselective Lewis base catalysis: b) S. E. Denmark, D. M. Coe, N. E. Pratt, B. D. Griedel, J. Org. Chem. 1994, 59, 6161; c) S. E. Denmark, J. Fu, J. Am. Chem. Soc. 2000, 122, 12021; d) S. E. Denmark, J. Fu, J. Am. Chem. Soc. 2001, 123, 9488; e) K. Iseki, Y. Kuroki, M. Takahashi, Y. Kobayashi, Tetrahedron Lett. 1996, 37, 5149; f) K. Iseki, Y. Kuroki, M. Takahashi, S. Kishimoto, Y. Kobayashi, Tetrahedron 1997, 53, 3513; g) K. Iseki, S. Mizuno, Y. Kuroki, Y. Kobayashi, Tetrahedron Lett. 1998, 39, 2767; h) K. Iseki, S. Mizuno, Y. Kuroki, Y. Kobayashi, Tetrahedron 1999, 55, 977; i) M. Nakajima, M. Saito, M. Shiro, S. Hashimoto, J. Am. Chem. Soc. 1998, 120, 6419; j) A. V. Malkov, M. Orsini, D. Pernazza, K. W. Muir, V. Langer, P. Meghani, P. Kocovsky, Org. Lett. 2002, 4, 1047.
19. For a recent review of enantioselective Lewis acid catalyzed allylmetal additions, see: a) A. Yanagisawa in Comprehensive Asymmetric Catalysis, Vol. II (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 1999, chap. 27. Enantioselective Lewis base catalysis: b) S. E. Denmark, D. M. Coe, N. E. Pratt, B. D. Griedel, J. Org. Chem. 1994, 59, 6161; c) S. E. Denmark, J. Fu, J. Am. Chem. Soc. 2000, 122, 12021; d) S. E. Denmark, J. Fu, J. Am. Chem. Soc. 2001, 123, 9488; e) K. Iseki, Y. Kuroki, M. Takahashi, Y. Kobayashi, Tetrahedron Lett. 1996, 37, 5149; f) K. Iseki, Y. Kuroki, M. Takahashi, S. Kishimoto, Y. Kobayashi, Tetrahedron 1997, 53, 3513; g) K. Iseki, S. Mizuno, Y. Kuroki, Y. Kobayashi, Tetrahedron Lett. 1998, 39, 2767; h) K. Iseki, S. Mizuno, Y. Kuroki, Y. Kobayashi, Tetrahedron 1999, 55, 977; i) M. Nakajima, M. Saito, M. Shiro, S. Hashimoto, J. Am. Chem. Soc. 1998, 120, 6419; j) A. V. Malkov, M. Orsini, D. Pernazza, K. W. Muir, V. Langer, P. Meghani, P. Kocovsky, Org. Lett. 2002, 4, 1047.
20. For a recent review of enantioselective Lewis acid catalyzed allylmetal additions, see: a) A. Yanagisawa in Comprehensive Asymmetric Catalysis, Vol. II (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 1999, chap. 27. Enantioselective Lewis base catalysis: b) S. E. Denmark, D. M. Coe, N. E. Pratt, B. D. Griedel, J. Org. Chem. 1994, 59, 6161; c) S. E. Denmark, J. Fu, J. Am. Chem. Soc. 2000, 122, 12021; d) S. E. Denmark, J. Fu, J. Am. Chem. Soc. 2001, 123, 9488; e) K. Iseki, Y. Kuroki, M. Takahashi, Y. Kobayashi, Tetrahedron Lett. 1996, 37, 5149; f) K. Iseki, Y. Kuroki, M. Takahashi, S. Kishimoto, Y. Kobayashi, Tetrahedron 1997, 53, 3513; g) K. Iseki, S. Mizuno, Y. Kuroki, Y. Kobayashi, Tetrahedron Lett. 1998, 39, 2767; h) K. Iseki, S. Mizuno, Y. Kuroki, Y. Kobayashi, Tetrahedron 1999, 55, 977; i) M. Nakajima, M. Saito, M. Shiro, S. Hashimoto, J. Am. Chem. Soc. 1998, 120, 6419; j) A. V. Malkov, M. Orsini, D. Pernazza, K. W. Muir, V. Langer, P. Meghani, P. Kocovsky, Org. Lett. 2002, 4, 1047.
21. For a recent review of enantioselective Lewis acid catalyzed allylmetal additions, see: a) A. Yanagisawa in Comprehensive Asymmetric Catalysis, Vol. II (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 1999, chap. 27. Enantioselective Lewis base catalysis: b) S. E. Denmark, D. M. Coe, N. E. Pratt, B. D. Griedel, J. Org. Chem. 1994, 59, 6161; c) S. E. Denmark, J. Fu, J. Am. Chem. Soc. 2000, 122, 12021; d) S. E. Denmark, J. Fu, J. Am. Chem. Soc. 2001, 123, 9488; e) K. Iseki, Y. Kuroki, M. Takahashi, Y. Kobayashi, Tetrahedron Lett. 1996, 37, 5149; f) K. Iseki, Y. Kuroki, M. Takahashi, S. Kishimoto, Y. Kobayashi, Tetrahedron 1997, 53, 3513; g) K. Iseki, S. Mizuno, Y. Kuroki, Y. Kobayashi, Tetrahedron Lett. 1998, 39, 2767; h) K. Iseki, S. Mizuno, Y. Kuroki, Y. Kobayashi, Tetrahedron 1999, 55, 977; i) M. Nakajima, M. Saito, M. Shiro, S. Hashimoto, J. Am. Chem. Soc. 1998, 120, 6419; j) A. V. Malkov, M. Orsini, D. Pernazza, K. W. Muir, V. Langer, P. Meghani, P. Kocovsky, Org. Lett. 2002, 4, 1047.
22. For a recent review of enantioselective Lewis acid catalyzed allylmetal additions, see: a) A. Yanagisawa in Comprehensive Asymmetric Catalysis, Vol. II (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 1999, chap. 27. Enantioselective Lewis base catalysis: b) S. E. Denmark, D. M. Coe, N. E. Pratt, B. D. Griedel, J. Org. Chem. 1994, 59, 6161; c) S. E. Denmark, J. Fu, J. Am. Chem. Soc. 2000, 122, 12021; d) S. E. Denmark, J. Fu, J. Am. Chem. Soc. 2001, 123, 9488; e) K. Iseki, Y. Kuroki, M. Takahashi, Y. Kobayashi, Tetrahedron Lett. 1996, 37, 5149; f) K. Iseki, Y. Kuroki, M. Takahashi, S. Kishimoto, Y. Kobayashi, Tetrahedron 1997, 53, 3513; g) K. Iseki, S. Mizuno, Y. Kuroki, Y. Kobayashi, Tetrahedron Lett. 1998, 39, 2767; h) K. Iseki, S. Mizuno, Y. Kuroki, Y. Kobayashi, Tetrahedron 1999, 55, 977; i) M. Nakajima, M. Saito, M. Shiro, S. Hashimoto, J. Am. Chem. Soc. 1998, 120, 6419; j) A. V. Malkov, M. Orsini, D. Pernazza, K. W. Muir, V. Langer, P. Meghani, P. Kocovsky, Org. Lett. 2002, 4, 1047.
23. For a recent review of enantioselective Lewis acid catalyzed allylmetal additions, see: a) A. Yanagisawa in Comprehensive Asymmetric Catalysis, Vol. II (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 1999, chap. 27. Enantioselective Lewis base catalysis: b) S. E. Denmark, D. M. Coe, N. E. Pratt, B. D. Griedel, J. Org. Chem. 1994, 59, 6161; c) S. E. Denmark, J. Fu, J. Am. Chem. Soc. 2000, 122, 12021; d) S. E. Denmark, J. Fu, J. Am. Chem. Soc. 2001, 123, 9488; e) K. Iseki, Y. Kuroki, M. Takahashi, Y. Kobayashi, Tetrahedron Lett. 1996, 37, 5149; f) K. Iseki, Y. Kuroki, M. Takahashi, S. Kishimoto, Y. Kobayashi, Tetrahedron 1997, 53, 3513; g) K. Iseki, S. Mizuno, Y. Kuroki, Y. Kobayashi, Tetrahedron Lett. 1998, 39, 2767; h) K. Iseki, S. Mizuno, Y. Kuroki, Y. Kobayashi, Tetrahedron 1999, 55, 977; i) M. Nakajima, M. Saito, M. Shiro, S. Hashimoto, J. Am. Chem. Soc. 1998, 120, 6419; j) A. V. Malkov, M. Orsini, D. Pernazza, K. W. Muir, V. Langer, P. Meghani, P. Kocovsky, Org. Lett. 2002, 4, 1047.
24. For a recent review of enantioselective Lewis acid catalyzed allylmetal additions, see: a) A. Yanagisawa in Comprehensive Asymmetric Catalysis, Vol. II (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 1999, chap. 27. Enantioselective Lewis base catalysis: b) S. E. Denmark, D. M. Coe, N. E. Pratt, B. D. Griedel, J. Org. Chem. 1994, 59, 6161; c) S. E. Denmark, J. Fu, J. Am. Chem. Soc. 2000, 122, 12021; d) S. E. Denmark, J. Fu, J. Am. Chem. Soc. 2001, 123, 9488; e) K. Iseki, Y. Kuroki, M. Takahashi, Y. Kobayashi, Tetrahedron Lett. 1996, 37, 5149; f) K. Iseki, Y. Kuroki, M. Takahashi, S. Kishimoto, Y. Kobayashi, Tetrahedron 1997, 53, 3513; g) K. Iseki, S. Mizuno, Y. Kuroki, Y. Kobayashi, Tetrahedron Lett. 1998, 39, 2767; h) K. Iseki, S. Mizuno, Y. Kuroki, Y. Kobayashi, Tetrahedron 1999, 55, 977; i) M. Nakajima, M. Saito, M. Shiro, S. Hashimoto, J. Am. Chem. Soc. 1998, 120, 6419; j) A. V. Malkov, M. Orsini, D. Pernazza, K. W. Muir, V. Langer, P. Meghani, P. Kocovsky, Org. Lett. 2002, 4, 1047.
25. J. W. A. Kinnaird, P. Y. Ng, K. Kubota, X. Wang, J. L. Leighton, J. Am. Chem. Soc. 2002, 124, 7920.
26. The cyclohexane diamine is treated with the appropriate substituted benzaldehyde to give the bis-Schiff base, which is reduced to the bis-(p-X-benzyl)diamine. The diamine is then treated with allyltrichlorosilane to give the active reagent. See the Supporting Information.
27. a) M. T. Reetz, K. Kesseler, A. Jung, Tetrahedron Lett. 1984, 25, 729. For a comprehensive discussion regarding the tendency of β-alkoxyalkanals to favor the anti diastereomer in allylation and aldol reactions, see: b) D. A. Evans, M. J. Dart, J. L. Duffy, M. G. Yang, J. Am. Chem. Soc. 1996, 118, 4322.
28. a) M. T. Reetz, K. Kesseler, A. Jung, Tetrahedron Lett. 1984, 25, 729. For a comprehensive discussion regarding the tendency of β-alkoxyalkanals to favor the anti diastereomer in allylation and aldol reactions, see: b) D. A. Evans, M. J. Dart, J. L. Duffy, M. G. Yang, J. Am. Chem. Soc. 1996, 118, 4322.