Asymmetric Reduction of Aromatic Ketones with Reagents Prepared from NaBH4 and ZnCl2 in the Presence of 1,2 : 5,6-Di-O-isopropylidene-α-d-glucofuranose
- 1 May 1981
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 54 (5) , 1424-1428
- https://doi.org/10.1246/bcsj.54.1424
Abstract
Asymmetric reduction of prochiral aromatic ketones using a freshly prepared complex derived from NaBH4, 1/3 equiv of ZnCl2, and 1,2 : 5,6-di-O-isopropylidene-α-D-glucofuranose (1) gives an excess of the corresponding (S)-alcohols in substantial optical yields (28–68%). The effects of the NaBH4/ZnCl2/1 ratio, temperature, solvent, structure of various monosaccharide derivatives, and the metal cation of the reagent on the optical yields were examined.Keywords
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