Regioselective hydrosilylation of propargylic alcohols: An aldol surrogate

Angewandte Chemie - International Edition

Volumn 42, Issue 29, 2003, Pages 3415-3418

  Trost, Barry M ^a   Ball, Zachary T ^a   Jöge, Thomas ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

Aldol products; Asymmetric synthesis; Hydrosilylation; Organosilanes; Ruthenium catalysis

Indexed keywords

CHEMICAL BONDS; DISSOCIATION; KETONES; OXIDATION; REACTION KINETICS; STEREOCHEMISTRY;

HYDROSILYLATION;

ALCOHOLS;

ALCOHOL DERIVATIVE; GAMMA HYDROXYVINYLSILANE; KETONE; PROPARGYLIC ALCOHOL; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; HYDRATION; HYDROSILYLATION; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

ALKYNES; CATALYSIS; CHEMISTRY, ORGANIC; CYCLIZATION; KETONES; MODELS, CHEMICAL; MOLECULAR STRUCTURE; SILANES; STEREOISOMERISM;

EID: 0043031390     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351587     Document Type: Article

References (36)

1. G. Frater, W. Guenther, U. Mueller, Helv. Chim. Acta 1989, 72, 1846.
2. For approaches to asymmetric aldol reactions of methyl alkyl ketones see: a) R. T. Ruck, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 2882; b) S. E. Denmark, R. A. Stavenger, J. Am. Chem. Soc. 2000, 122, 8837; c) N. Yoshikawa, Y. M. A. Yamada, J. Das, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 468; d) A. Yanagisawa, Y. Matsumoto, H. Nakashima, K. Asakawa, H. Yamamoto, J. Am. Chem. Soc. 1997, 119, 9319; e) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1993, 115, 7039; g) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907; for reviews see h) E. M. Carreira, in Catalytic Asymmetric Synthesis, 2nd Ed. (Ed: I. Ojima), Wiley-VCH, New York, 2000, Ch. 8-2; i) B. List, Tetrahedron 2002, 58, 5573; j) S. G. Nelson, Tetrahedron: Asymmetry 1998, 9, 357.
3. For approaches to asymmetric aldol reactions of methyl alkyl ketones see: a) R. T. Ruck, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 2882; b) S. E. Denmark, R. A. Stavenger, J. Am. Chem. Soc. 2000, 122, 8837; c) N. Yoshikawa, Y. M. A. Yamada, J. Das, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 468; d) A. Yanagisawa, Y. Matsumoto, H. Nakashima, K. Asakawa, H. Yamamoto, J. Am. Chem. Soc. 1997, 119, 9319; e) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1993, 115, 7039; g) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907; for reviews see h) E. M. Carreira, in Catalytic Asymmetric Synthesis, 2nd Ed. (Ed: I. Ojima), Wiley-VCH, New York, 2000, Ch. 8-2; i) B. List, Tetrahedron 2002, 58, 5573; j) S. G. Nelson, Tetrahedron: Asymmetry 1998, 9, 357.
4. For approaches to asymmetric aldol reactions of methyl alkyl ketones see: a) R. T. Ruck, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 2882; b) S. E. Denmark, R. A. Stavenger, J. Am. Chem. Soc. 2000, 122, 8837; c) N. Yoshikawa, Y. M. A. Yamada, J. Das, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 468; d) A. Yanagisawa, Y. Matsumoto, H. Nakashima, K. Asakawa, H. Yamamoto, J. Am. Chem. Soc. 1997, 119, 9319; e) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1993, 115, 7039; g) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907; for reviews see h) E. M. Carreira, in Catalytic Asymmetric Synthesis, 2nd Ed. (Ed: I. Ojima), Wiley-VCH, New York, 2000, Ch. 8-2; i) B. List, Tetrahedron 2002, 58, 5573; j) S. G. Nelson, Tetrahedron: Asymmetry 1998, 9, 357.
5. For approaches to asymmetric aldol reactions of methyl alkyl ketones see: a) R. T. Ruck, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 2882; b) S. E. Denmark, R. A. Stavenger, J. Am. Chem. Soc. 2000, 122, 8837; c) N. Yoshikawa, Y. M. A. Yamada, J. Das, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 468; d) A. Yanagisawa, Y. Matsumoto, H. Nakashima, K. Asakawa, H. Yamamoto, J. Am. Chem. Soc. 1997, 119, 9319; e) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1993, 115, 7039; g) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907; for reviews see h) E. M. Carreira, in Catalytic Asymmetric Synthesis, 2nd Ed. (Ed: I. Ojima), Wiley-VCH, New York, 2000, Ch. 8-2; i) B. List, Tetrahedron 2002, 58, 5573; j) S. G. Nelson, Tetrahedron: Asymmetry 1998, 9, 357.
6. For approaches to asymmetric aldol reactions of methyl alkyl ketones see: a) R. T. Ruck, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 2882; b) S. E. Denmark, R. A. Stavenger, J. Am. Chem. Soc. 2000, 122, 8837; c) N. Yoshikawa, Y. M. A. Yamada, J. Das, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 468; d) A. Yanagisawa, Y. Matsumoto, H. Nakashima, K. Asakawa, H. Yamamoto, J. Am. Chem. Soc. 1997, 119, 9319; e) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1993, 115, 7039; g) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907; for reviews see h) E. M. Carreira, in Catalytic Asymmetric Synthesis, 2nd Ed. (Ed: I. Ojima), Wiley-VCH, New York, 2000, Ch. 8-2; i) B. List, Tetrahedron 2002, 58, 5573; j) S. G. Nelson, Tetrahedron: Asymmetry 1998, 9, 357.
7. For approaches to asymmetric aldol reactions of methyl alkyl ketones see: a) R. T. Ruck, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 2882; b) S. E. Denmark, R. A. Stavenger, J. Am. Chem. Soc. 2000, 122, 8837; c) N. Yoshikawa, Y. M. A. Yamada, J. Das, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 468; d) A. Yanagisawa, Y. Matsumoto, H. Nakashima, K. Asakawa, H. Yamamoto, J. Am. Chem. Soc. 1997, 119, 9319; e) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1993, 115, 7039; g) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907; for reviews see h) E. M. Carreira, in Catalytic Asymmetric Synthesis, 2nd Ed. (Ed: I. Ojima), Wiley-VCH, New York, 2000, Ch. 8-2; i) B. List, Tetrahedron 2002, 58, 5573; j) S. G. Nelson, Tetrahedron: Asymmetry 1998, 9, 357.
8. For approaches to asymmetric aldol reactions of methyl alkyl ketones see: a) R. T. Ruck, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 2882; b) S. E. Denmark, R. A. Stavenger, J. Am. Chem. Soc. 2000, 122, 8837; c) N. Yoshikawa, Y. M. A. Yamada, J. Das, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 468; d) A. Yanagisawa, Y. Matsumoto, H. Nakashima, K. Asakawa, H. Yamamoto, J. Am. Chem. Soc. 1997, 119, 9319; e) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1993, 115, 7039; g) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907; for reviews see h) E. M. Carreira, in Catalytic Asymmetric Synthesis, 2nd Ed. (Ed: I. Ojima), Wiley-VCH, New York, 2000, Ch. 8-2; i) B. List, Tetrahedron 2002, 58, 5573; j) S. G. Nelson, Tetrahedron: Asymmetry 1998, 9, 357.
9. For approaches to asymmetric aldol reactions of methyl alkyl ketones see: a) R. T. Ruck, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 2882; b) S. E. Denmark, R. A. Stavenger, J. Am. Chem. Soc. 2000, 122, 8837; c) N. Yoshikawa, Y. M. A. Yamada, J. Das, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 468; d) A. Yanagisawa, Y. Matsumoto, H. Nakashima, K. Asakawa, H. Yamamoto, J. Am. Chem. Soc. 1997, 119, 9319; e) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1993, 115, 7039; g) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907; for reviews see h) E. M. Carreira, in Catalytic Asymmetric Synthesis, 2nd Ed. (Ed: I. Ojima), Wiley-VCH, New York, 2000, Ch. 8-2; i) B. List, Tetrahedron 2002, 58, 5573; j) S. G. Nelson, Tetrahedron: Asymmetry 1998, 9, 357.
10. For approaches to asymmetric aldol reactions of methyl alkyl ketones see: a) R. T. Ruck, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 2882; b) S. E. Denmark, R. A. Stavenger, J. Am. Chem. Soc. 2000, 122, 8837; c) N. Yoshikawa, Y. M. A. Yamada, J. Das, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 468; d) A. Yanagisawa, Y. Matsumoto, H. Nakashima, K. Asakawa, H. Yamamoto, J. Am. Chem. Soc. 1997, 119, 9319; e) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1993, 115, 7039; g) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907; for reviews see h) E. M. Carreira, in Catalytic Asymmetric Synthesis, 2nd Ed. (Ed: I. Ojima), Wiley-VCH, New York, 2000, Ch. 8-2; i) B. List, Tetrahedron 2002, 58, 5573; j) S. G. Nelson, Tetrahedron: Asymmetry 1998, 9, 357.
11. For approaches to asymmetric aldol reactions of methyl alkyl ketones see: a) R. T. Ruck, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 2882; b) S. E. Denmark, R. A. Stavenger, J. Am. Chem. Soc. 2000, 122, 8837; c) N. Yoshikawa, Y. M. A. Yamada, J. Das, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 468; d) A. Yanagisawa, Y. Matsumoto, H. Nakashima, K. Asakawa, H. Yamamoto, J. Am. Chem. Soc. 1997, 119, 9319; e) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649; f) K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1993, 115, 7039; g) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907; for reviews see h) E. M. Carreira, in Catalytic Asymmetric Synthesis, 2nd Ed. (Ed: I. Ojima), Wiley-VCH, New York, 2000, Ch. 8-2; i) B. List, Tetrahedron 2002, 58, 5573; j) S. G. Nelson, Tetrahedron: Asymmetry 1998, 9, 357.
12. T. Ohkuma, M. Kitamura, R. Noyori, in Catalytic Asymmetric Synthesis 2nd Ed. (Ed: I. Ojima), Wiley-VCH, New York, 2000, Ch. 1.
13. a) D. E. Frantz, R. Fassler, E. M. Carreira, J. Am. Chem. Soc. 2000, 122, 1806-1807;
14. b) N. K. Anand, E. M. Carreira, J. Am. Chem. Soc. 2001, 123, 9687-9688;
15. c) D. Boyall, D. E. Frantz, E. M. Carreira, Org. Lett. 2002, 4, 2605-2606.
16. For a recent example of catalyzed alkyne hydration see a) E. Mizushima, K. Sato, T. Hayashi, M. Tanaka, Angew. Chem. Int. Ed. 2002, 41, 4563; b) E. Mizushima, K. Sato, T. Hayashi, Angew. Chem. 2002, 114, 4745.
17. For a recent example of catalyzed alkyne hydration see a) E. Mizushima, K. Sato, T. Hayashi, M. Tanaka, Angew. Chem. Int. Ed. 2002, 41, 4563; b) E. Mizushima, K. Sato, T. Hayashi, Angew. Chem. 2002, 114, 4745.
18. a) B. M. Trost, Z. T. Ball, T. Joege, J. Am. Chem. Soc. 2002, 124, 7922-7923;
19. b) B. M. Trost, Z. T. Ball, J. Am. Chem. Soc. 2001, 123, 12726-12727.
20. Intermolecular hydrosilylation of internal alkynes: a) G. A. Molander, W. H. Retsch, Organometallics 1995, 14, 4570-4575; for instances of selective hydrosilylation of propargylic alcohols: b) D. Humiliere, S. Thorimbert, M. Malacria, Synlett 1998, 1255; c) M. Isobe, R. Nishizawa, T. Nishikawa, K. Yoza, Tetrahedron Lett. 1999, 40, 6927-6932; d) K. Kahle, P. J. Murphy, J. Scott, R. Tamagni, J. Chem. Soc. Perkin Trans. 1 1997, 997-999; e) P. J. Murphy, J. L. Spencer, G. Procter, Tetrahedron Lett. 1990, 31, 1051-1054.
21. Intermolecular hydrosilylation of internal alkynes: a) G. A. Molander, W. H. Retsch, Organometallics 1995, 14, 4570-4575; for instances of selective hydrosilylation of propargylic alcohols: b) D. Humiliere, S. Thorimbert, M. Malacria, Synlett 1998, 1255; c) M. Isobe, R. Nishizawa, T. Nishikawa, K. Yoza, Tetrahedron Lett. 1999, 40, 6927-6932; d) K. Kahle, P. J. Murphy, J. Scott, R. Tamagni, J. Chem. Soc. Perkin Trans. 1 1997, 997-999; e) P. J. Murphy, J. L. Spencer, G. Procter, Tetrahedron Lett. 1990, 31, 1051-1054.
22. Intermolecular hydrosilylation of internal alkynes: a) G. A. Molander, W. H. Retsch, Organometallics 1995, 14, 4570-4575; for instances of selective hydrosilylation of propargylic alcohols: b) D. Humiliere, S. Thorimbert, M. Malacria, Synlett 1998, 1255; c) M. Isobe, R. Nishizawa, T. Nishikawa, K. Yoza, Tetrahedron Lett. 1999, 40, 6927-6932; d) K. Kahle, P. J. Murphy, J. Scott, R. Tamagni, J. Chem. Soc. Perkin Trans. 1 1997, 997-999; e) P. J. Murphy, J. L. Spencer, G. Procter, Tetrahedron Lett. 1990, 31, 1051-1054.
23. Intermolecular hydrosilylation of internal alkynes: a) G. A. Molander, W. H. Retsch, Organometallics 1995, 14, 4570-4575; for instances of selective hydrosilylation of propargylic alcohols: b) D. Humiliere, S. Thorimbert, M. Malacria, Synlett 1998, 1255; c) M. Isobe, R. Nishizawa, T. Nishikawa, K. Yoza, Tetrahedron Lett. 1999, 40, 6927-6932; d) K. Kahle, P. J. Murphy, J. Scott, R. Tamagni, J. Chem. Soc. Perkin Trans. 1 1997, 997-999; e) P. J. Murphy, J. L. Spencer, G. Procter, Tetrahedron Lett. 1990, 31, 1051-1054.
24. Intermolecular hydrosilylation of internal alkynes: a) G. A. Molander, W. H. Retsch, Organometallics 1995, 14, 4570-4575; for instances of selective hydrosilylation of propargylic alcohols: b) D. Humiliere, S. Thorimbert, M. Malacria, Synlett 1998, 1255; c) M. Isobe, R. Nishizawa, T. Nishikawa, K. Yoza, Tetrahedron Lett. 1999, 40, 6927-6932; d) K. Kahle, P. J. Murphy, J. Scott, R. Tamagni, J. Chem. Soc. Perkin Trans. 1 1997, 997-999; e) P. J. Murphy, J. L. Spencer, G. Procter, Tetrahedron Lett. 1990, 31, 1051-1054.
25. Intramolecular hydrosilylation: a) B. M. Trost, Z. T. Ball, J. Am. Chem. Soc. 2003, 125, 30-31;
26. b) S. E. Denmark, S. Pan, Org. Lett. 2002, 4, 4163-4166;
27. c) J. A. Marshall, M. M. Yanik, Org. Lett. 2000, 2, 2173-2175;
28. d) K. Tamao, K. Maeda, T. Tanaka, Y. Ito, Tetrahedron Lett. 1988, 29, 6955-6956.
29. The intramolecular hydrosilylation of homopropargylic alcohols has also been used to create β-hydroxy ketones. In that case elimination from the initial enol is not possible, and the vinylsilane intermediate does not allow functionalization at the α-carbon. See refs. [8c, d].
30. K. Miura, T. Hondo, T. Takahashi, A. Hosomi, Tetrahedron Lett. 2000, 41, 2129-2132; K. Miura, T. Hondo, T. Nakagawa, T. Takahashi, A. Hosomi, Org. Lett. 2000, 2, 385-388.
31. K. Miura, T. Hondo, T. Takahashi, A. Hosomi, Tetrahedron Lett. 2000, 41, 2129-2132; K. Miura, T. Hondo, T. Nakagawa, T. Takahashi, A. Hosomi, Org. Lett. 2000, 2, 385-388.
32. M. Shimizu, M. Kawamoto, Y. Niwa, Chem. Commun. 1999, 1151-1152.
33. K. T. Mead, Tetrahedron Lett. 1987, 28, 1019-1022.
34. H. Tomioka, T. Suzuki, K. Oshima, H. Nozaki, Tetrahedron Lett. 1982, 23, 3387-3390; I. Hasan, Y. Kishi, Tetrahedron Lett. 1980, 21, 4229-4232.
35. H. Tomioka, T. Suzuki, K. Oshima, H. Nozaki, Tetrahedron Lett. 1982, 23, 3387-3390; I. Hasan, Y. Kishi, Tetrahedron Lett. 1980, 21, 4229-4232.
36. For a report on the oxidation of α,β-epoxysilanes: K. Tamao, K. Maeda, Tetrahedron Lett. 1986, 27, 65-68.