Release Time:2019-03-09  Hits:

Indexed by: Journal Article

Date of Publication: 2014-05-19

Journal: SYNTHETIC COMMUNICATIONS

Included Journals: Scopus、SCIE

Volume: 44

Issue: 10

Page Number: 1515-1520

ISSN: 0039-7911

Key Words: chiral oxazaborolidine; chiral alcohols; dimethyl sulfate; Asymmetric reduction; sodium borohydride

Abstract: The enantioselective reduction of prochiral ketones with NaBH4/Me2SO4/(S)-Me-CBS is described. Borane is generated in situ via the reaction of NaBH4 with Me2SO4 in tetrahydrofuran, which is as efficient as the commercial one. Such in situ-generated borane reagent was applied to reduce prochiral ketones in the presence of chiral oxazaborolidine catalyst directly. The corresponding chiral secondary alcohols were obtained with excellent enantiomeric excesses (93-99% ee) and good to excellent yield (80-99%).