Enantioselective reduction of esters: Synthesis of optically active α- acetoxy ethers

Tetrahedron Letters

Volumn 41, Issue 19, 2000, Pages 3593-3596

  Rychnovsky, Scott D ^a   Bax, Brian M ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPHEDRINE DERIVATIVE; ESTER DERIVATIVE; ETHER DERIVATIVE;

ACETYLATION; ARTICLE; CHEMICAL REACTION; ENANTIOMER; REDUCTION; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS;

EID: 0034612127     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00470-6     Document Type: Article

References (16)

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4. This conclusion was further supported by a negative cross-over experiment: unpublished work, Sinz, C.; Rychnovsky, S. D.
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10. 4: C, 65.53; H, 7.61. Found: C, 65.77; H, 7.41. The product was determined to be 83% ee by analysis on a CHIRACEL OJ column (hexane:2-propanol=97:3 at a flow rate of 0.8 ml/min). The retention times were 12.5 min for the minor R-enantiomer and 13.5 min for the major S-enantiomer.
11. Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kuhnle, F. N. M. J. Org. Chem. 1995, 60, 1788-1799.
12. Noyori, R.; Tomino, I.; Yamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6709-6716.
13. 4 and lower yields and % ee, perhaps due to adventitious water.
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16. Both the sign and the magnitude of the optical rotations for the two samples of compound 8, prepared in Table 1 and in Scheme 2, are consistent with them having the same absolute configuration. Both samples also showed the same retention time on a Chiracel OJ column.