STEREOCONTROLLED CATALYTIC ASYMMETRIC REDUCTION OF KETONES WITH OXAZABOROLIDINES DERIVED FROM NEW CHIRAL AMINO-ALCOHOLS

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The highly stereocontrolled enantioselective reduction of ketones in the presence of catalytic amounts of new chiral (S)-beta-amino alcohols 1 and 2 with borane in THF at -78-degrees-C proceeds in high chemical and optical yields; secondary alcohols with the R-configuration are obtained in the presence of 1b, but secondary alcohols with the S-configuration are obtained in the presence of 2a.
Publisher
AMER CHEMICAL SOC
Issue Date
1993-08
Language
English
Article Type
Letter
Keywords

PROCHIRAL AROMATIC KETONES; ENANTIOSELECTIVE REDUCTION; MODIFIED BOROHYDRIDES; OXIME ETHERS; BORANE; AMINOALCOHOLS; MECHANISM; EFFICIENT; REAGENTS

Citation

JOURNAL OF ORGANIC CHEMISTRY, v.58, no.17, pp.4511 - 4512

ISSN
0022-3263
DOI
10.1021/jo00069a002
URI
http://hdl.handle.net/10203/64280
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