Stereochemistry of the thermal isomerizations of trans-1-ethenyl-2-phenylcyclopropane to 4-phenylcyclopentene

Journal of the American Chemical Society

Volumn 118, Issue 35, 1996, Pages 8258-8265

  Baldwin, John E ^a   Bonacorsi Jr , Samuel J ^a  

^a SYRACUSE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029814160     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9613771     Document Type: Article

References (53)

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47. Vinylcyclopropanes substituted with a tert-butyl group at C1′ appear to react with other stereochemical characteristics; see: (a) Gajewski, J. J.; Warner, J. M. J. Am. Chem. Soc. 1984, 106, 802-803. (b) Gajewski, J. J.; Squicciarini, M. P. J. Am. Chem. Soc. 1989, 111, 6717-6728. (c) Gajewski, J. J.; Olson, L. P. J. Am. Chem. Soc. 1991, 113, 7432-7433. (d) Gajewski, J. J.; Olson, L. P.; Willcott, M. R. J. Am. Chem. Soc. 1996, 118, 299-306.
48. Vinylcyclopropanes substituted with a tert-butyl group at C1′ appear to react with other stereochemical characteristics; see: (a) Gajewski, J. J.; Warner, J. M. J. Am. Chem. Soc. 1984, 106, 802-803. (b) Gajewski, J. J.; Squicciarini, M. P. J. Am. Chem. Soc. 1989, 111, 6717-6728. (c) Gajewski, J. J.; Olson, L. P. J. Am. Chem. Soc. 1991, 113, 7432-7433. (d) Gajewski, J. J.; Olson, L. P.; Willcott, M. R. J. Am. Chem. Soc. 1996, 118, 299-306.
49. Vinylcyclopropanes substituted with a tert-butyl group at C1′ appear to react with other stereochemical characteristics; see: (a) Gajewski, J. J.; Warner, J. M. J. Am. Chem. Soc. 1984, 106, 802-803. (b) Gajewski, J. J.; Squicciarini, M. P. J. Am. Chem. Soc. 1989, 111, 6717-6728. (c) Gajewski, J. J.; Olson, L. P. J. Am. Chem. Soc. 1991, 113, 7432-7433. (d) Gajewski, J. J.; Olson, L. P.; Willcott, M. R. J. Am. Chem. Soc. 1996, 118, 299-306.
50. Compare Carpenter, B. K. Acc. Chem. Res. 1992, 25, 520-528.
51. From this rotation, one may conclude that the ee of the ketone is at least 56-58%; see: (a) Taber, D. F.; Raman, K. J. Am. Chem. Soc. 1983, 105, 5935-5937, note 13. (b) Taura, Y.; Tanaka, M.; Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron 1991, 47, 4879-4888.
52. From this rotation, one may conclude that the ee of the ketone is at least 56-58%; see: (a) Taber, D. F.; Raman, K. J. Am. Chem. Soc. 1983, 105, 5935-5937, note 13. (b) Taura, Y.; Tanaka, M.; Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron 1991, 47, 4879-4888.
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