Asymmetric Synthesis Using Chirally Modified Borohydrides. Part 3. Enantioselective Reduction of Ketones and Oxime Ethers with Reagents Prepared from Borane and Chiral Amino Alcohols

DOI: 10.1039/P19850002039

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2039 - 2044 (1985)

Update date:2022-08-04

Topics:

Authors:

Itsuno, Shinichi

Nakano, Michio

Miyazaki, Koji

Masuda, Hirofumi

Ito, Koichi

et al. et al.

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Article abstract of DOI:10.1039/P19850002039

The asymmetric reduction of aromatic and aliphatic ketones, halogeno 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. 90percent e.e.) were obtained in the reduction of various ketones and oxime ethers.

Full text of DOI:10.1039/P19850002039

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