Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Chemoselective Reduction of Phenyl Ketones with Amino Alcohol–Borane Complexes
Shinichi ItsunoTakashi WakasugiKoichi ItoAkira HiraoSeiichi Nakahama
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1985 Volume 58 Issue 6 Pages 1669-1673

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Abstract

A new reducing agent was prepared from borane and amino alcohols. The reagent is very effective for chemoselective reduction of ketones in the presence of esters, oxime ethers, tertiary amides, nitriles, halides, and acyl chlorides. The polymeric reagent prepared from borane and polymer-supported amino alcohol was also prepared easily. Aldehydes are highly selectively reduced to primary alcohols in the presence of ketone with the polymeric reagent. Simple filtration separated cleanly the unchanged ketone from the polymeric reagent which gave, after hydrolysis, only primary alcohol as the product. The polymeric reagent was regenerated by treatment with borane and could be reused.

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