Tetrahedron

Influnce des interactions de torsion dans la reduction des cetones par les hydrures interpretation generale du deroulement sterique de la reduction des cetones …

M Cherest, N Prudent

Index: Cherest, M.; Prudent, N. Tetrahedron, 1980 , vol. 36, p. 1599 - 1606

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Citation Number: 27

Abstract

Reduction of ketones L-CHMe-CO-R [L= Ph and Cy (Cy= cyclohexyl) and R= Me, Et, iPr and tBu] affords pairs of diastereoisomeric alcohols L-CHMe-CHOH-R. The predominant diastereoisomer is always that predicted by Cram's rule, and the stereoselectivity of the reaction generally increases as R is made more bulky. Thus, with LiAlH4 in ether at 35°, the diastereoisomer ratios are respectively 2.8: 1, 3.2: 1, 5.0: 1, and 49: 1 when L= Ph and 1.6: ...