Diastereoselective Aldol Reactions of Enolates Generated from Vicinally Substituted Trimethylsilylmethyl Cyclopropyl Ketones

Organic Letters

Volumn 5, Issue 23, 2003, Pages 4281-4284

  Yadav, Veejendra K ^a   Balamurugan, Rengarajan ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; KETONE DERIVATIVE; LEWIS ACID; TETRAHYDROFURAN DERIVATIVE;

ADDITION REACTION; ALDOL REACTION; ARTICLE; DIASTEREOISOMER; RING OPENING; STEREOCHEMISTRY;

EID: 0344065761     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035481g     Document Type: Article

References (54)

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34. 1H chemical shifts of the hydrogen on the carbinol carbon. The hydrogen resonated 0.06-0.12 ppm downfield in the syn isomer compared to the hydrogen in the corresponding anti isomer. Furthermore, this hydrogen appeared as a triplet (J = 1.7-6.3 Hz) and a doublet (J = 4.6-5.8 Hz) or a broad singlet, respectively, in the anti and syn aldol products obtained from arylaldehydes. For references related to the syn and anti assignments, see: (a) Ohtsuka, Y.; Koyasu, K.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 2543. (b) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333. (c) Hasegawa, E.; Ishiyama, K.; Kato, T.; Horaguchi, T.; Shimizu, T.; Tanaka, S.; Yamashita, Y. J. Org. Chem. 1992, 57, 5352. (d) Noyori, R.; Nishida, I.; Sakata, J. J. Am. Chem. Soc. 1981, 103, 2106. (e) House, H. O.; Crumrine, D. S. ; Teranishi, A. Y.; Olmstead, H. D. J. Am. Chem. Soc. 1973, 95, 3310.
35. 1H chemical shifts of the hydrogen on the carbinol carbon. The hydrogen resonated 0.06-0.12 ppm downfield in the syn isomer compared to the hydrogen in the corresponding anti isomer. Furthermore, this hydrogen appeared as a triplet (J = 1.7-6.3 Hz) and a doublet (J = 4.6-5.8 Hz) or a broad singlet, respectively, in the anti and syn aldol products obtained from arylaldehydes. For references related to the syn and anti assignments, see: (a) Ohtsuka, Y.; Koyasu, K.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 2543. (b) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333. (c) Hasegawa, E.; Ishiyama, K.; Kato, T.; Horaguchi, T.; Shimizu, T.; Tanaka, S.; Yamashita, Y. J. Org. Chem. 1992, 57, 5352. (d) Noyori, R.; Nishida, I.; Sakata, J. J. Am. Chem. Soc. 1981, 103, 2106. (e) House, H. O.; Crumrine, D. S. ; Teranishi, A. Y.; Olmstead, H. D. J. Am. Chem. Soc. 1973, 95, 3310.
36. 1H chemical shifts of the hydrogen on the carbinol carbon. The hydrogen resonated 0.06-0.12 ppm downfield in the syn isomer compared to the hydrogen in the corresponding anti isomer. Furthermore, this hydrogen appeared as a triplet (J = 1.7-6.3 Hz) and a doublet (J = 4.6-5.8 Hz) or a broad singlet, respectively, in the anti and syn aldol products obtained from arylaldehydes. For references related to the syn and anti assignments, see: (a) Ohtsuka, Y.; Koyasu, K.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 2543. (b) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333. (c) Hasegawa, E.; Ishiyama, K.; Kato, T.; Horaguchi, T.; Shimizu, T.; Tanaka, S.; Yamashita, Y. J. Org. Chem. 1992, 57, 5352. (d) Noyori, R.; Nishida, I.; Sakata, J. J. Am. Chem. Soc. 1981, 103, 2106. (e) House, H. O.; Crumrine, D. S. ; Teranishi, A. Y.; Olmstead, H. D. J. Am. Chem. Soc. 1973, 95, 3310.
37. 1H chemical shifts of the hydrogen on the carbinol carbon. The hydrogen resonated 0.06-0.12 ppm downfield in the syn isomer compared to the hydrogen in the corresponding anti isomer. Furthermore, this hydrogen appeared as a triplet (J = 1.7-6.3 Hz) and a doublet (J = 4.6-5.8 Hz) or a broad singlet, respectively, in the anti and syn aldol products obtained from arylaldehydes. For references related to the syn and anti assignments, see: (a) Ohtsuka, Y.; Koyasu, K.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 2543. (b) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333. (c) Hasegawa, E.; Ishiyama, K.; Kato, T.; Horaguchi, T.; Shimizu, T.; Tanaka, S.; Yamashita, Y. J. Org. Chem. 1992, 57, 5352. (d) Noyori, R.; Nishida, I.; Sakata, J. J. Am. Chem. Soc. 1981, 103, 2106. (e) House, H. O.; Crumrine, D. S. ; Teranishi, A. Y.; Olmstead, H. D. J. Am. Chem. Soc. 1973, 95, 3310.
38. 1H chemical shifts of the hydrogen on the carbinol carbon. The hydrogen resonated 0.06-0.12 ppm downfield in the syn isomer compared to the hydrogen in the corresponding anti isomer. Furthermore, this hydrogen appeared as a triplet (J = 1.7-6.3 Hz) and a doublet (J = 4.6-5.8 Hz) or a broad singlet, respectively, in the anti and syn aldol products obtained from arylaldehydes. For references related to the syn and anti assignments, see: (a) Ohtsuka, Y.; Koyasu, K.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 2543. (b) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333. (c) Hasegawa, E.; Ishiyama, K.; Kato, T.; Horaguchi, T.; Shimizu, T.; Tanaka, S.; Yamashita, Y. J. Org. Chem. 1992, 57, 5352. (d) Noyori, R.; Nishida, I.; Sakata, J. J. Am. Chem. Soc. 1981, 103, 2106. (e) House, H. O.; Crumrine, D. S. ; Teranishi, A. Y.; Olmstead, H. D. J. Am. Chem. Soc. 1973, 95, 3310.
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49. For transition state models, see: (a) Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920. (b) Dubois, J. E.; Fellmann, P. Tetrahedron Lett. 1975, 1225. (c) Fellmann, P.; Dubois, J. E. Tetrahedron 1978, 34, 1349. (d) Evans, D. A.; Nelson, J. V.; Taber, T. R. Topics in Stereochemistry; Eliel, E. L., Wiley, S. H., Eds.; Wiley-Interscience: New York, 1982; Vol. 13, p 1. (e) Also see ref 10.
50. For transition state models, see: (a) Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920. (b) Dubois, J. E.; Fellmann, P. Tetrahedron Lett. 1975, 1225. (c) Fellmann, P.; Dubois, J. E. Tetrahedron 1978, 34, 1349. (d) Evans, D. A.; Nelson, J. V.; Taber, T. R. Topics in Stereochemistry; Eliel, E. L., Wiley, S. H., Eds.; Wiley-Interscience: New York, 1982; Vol. 13, p 1. (e) Also see ref 10.
51. For transition state models, see: (a) Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920. (b) Dubois, J. E.; Fellmann, P. Tetrahedron Lett. 1975, 1225. (c) Fellmann, P.; Dubois, J. E. Tetrahedron 1978, 34, 1349. (d) Evans, D. A.; Nelson, J. V.; Taber, T. R. Topics in Stereochemistry; Eliel, E. L., Wiley, S. H., Eds.; Wiley-Interscience: New York, 1982; Vol. 13, p 1. (e) Also see ref 10.
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54. For alternative syntheses of similar substituted tetrahydrofuranylmethanol derivatives, see: (a) Hopkins, M. H.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 4748. (b) Hopkins, M. H.; Overman, L. E.; Rishton, G. M. J. Am. Chem. Soc. 1991, 113, 5354.