Asymmetric synthesis of 4,4-disubstituted-2-cyclohexen-1-ones from a chiral 2-(trimethylsilyl)benzamide

Tetrahedron Letters

Volumn 38, Issue 31, 1997, Pages 5433-5436

  Schultz, Arthur G ^a   Pettus, Liping ^a  

^a RENSSELAER POLYTECHNIC INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; CYCLOHEXENE DERIVATIVE;

ALKYLATION; ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030792352     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01215-X     Document Type: Article

References (17)

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2. For examples of the conversion of 1 and substituted analogues 1 to 2,5-cyclohexadien-1-ones, see: (a) Schultz, A. G.; Malachowski, W. P.; Pan, Y. J. Org. Chem. 1997, 62, 1223-1229.
3. (b) Schultz A. G.; Taveras, A. G.; Taylor, R. E.; Tham, F. S.; Kullnig, R. K. J. Am. Chem. Soc. 1992, 114, 8725-8727.
4. (c) Schultz, A. G.; Taveras, A. G.; Harrington, R. E. Tetrahedron Lett. 1988, 29, 3907-3910.
5. (d) Schultz, A. G.; Plummer, M.; Taveras, A. G.; Kullnig, R. K. J. Am. Chem. Soc. 1988, 110, 5547-5555.
6. The 2-(trimethylsilyl)benzarnide 4 was prepared from 2-(trimethylsilyl)benzoic acid and (S)-prolinol in 88% yield. For the preparation of 2-(trimethylsilyl)benzoic acid, see: Schultz, A. G.; Antoulinakis, E. G. J. Org. Chem. 1996, 61, 4555-4559.
7. 13C NMR, IR, low resolution MS and combustion analyses.
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14. 3).
15. (a) Schultz, A. G.; Macielag, M.; Sundararaman, P.; Taveras, A. G.; Welch, M. J. Am. Chem. Soc. 1988, 110, 7828-7841.
16. (b) Schultz, A. G. Chinese Chem. Soc. (Taiwan) 1994, 41, 487-495.
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