Asymmetric synthesis using chirally modified borohydrides. Part 3. Enantioselective reduction of ketones and oxime ethers with reagents prepared from borane and chiral amino alcohols
- 1 January 1985
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 2039-2044
- https://doi.org/10.1039/p19850002039
Abstract
The asymmetric reduction of aromatic and aliphatic ketones, halogeno ketones, hydroxy ketones, keto esters, and ketone oxime ethers with reagents prepared from borane and chiral amino alcohols has been investigated. When α,α-diphenyl β-amino alcohols, such as (2S,3R)-(–)-2-amino-3-methyl-1,1 -diphenylpentanol (2d), were used as a chiral auxiliary, very high enantioselectivities (ca. 90 % e.e.) were obtained in the reduction of various ketones and oxime ethers.This publication has 1 reference indexed in Scilit:
- A New Synthetic Route to (±)‐PerhydrohistrionicotoxinHelvetica Chimica Acta, 1977