Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Asymmetric Reduction of Schiff’s Bases with Lithium Aluminium Hydride–Monosaccharide Complexes to Give Optically Active Secondary Amines
Stephen R. LandorOlatunji O. SonolaAustin R. Tatchell
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1984 Volume 57 Issue 6 Pages 1658-1661

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Abstract

The asymmetric reduction of selected Schiff ’s bases (ketimines) with the lithium aluminium hydride–monosaccharide complexes derived from 3-O-benzyl-1,2-O-cyclohexylidene-α-D-glucofuranose gives optically active secondary amines. The absolute configuration of N-(1-phenylethyl)aniline was assigned as S by N-phenylation of S-(−)-1-phenylethylamine and hence all the levo-rotatory secondary amines obtained by this asymmetric reduction are assigned the S-configuration.

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