Release Time:2019-03-09  Hits:

Indexed by: Journal Article

Date of Publication: 2010-12-01

Journal: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Included Journals: Scopus、SCIE

Issue: 34

Page Number: 6525-6530

ISSN: 1434-193X

Key Words: Asymmetric catalysis; Phase-transfer catalysis; Hydroxylation; beta-Oxo esters

Abstract: The first enantioselective direct alpha-hydroxylation of beta-oxo esters was developed by using phase-transfer catalysis. 1-Indanone-derived 1-adamantyl (1-Ad) beta-oxo esters, in the presence of commercially available cumyl hydroperoxide and a cinchonine-based ammonium salt, resulted in the corresponding products with 69-91% yield and 65-74% ee. The reaction had also been successfully scaled-up to a gram quantity, and a similar yield was obtained without loss of the enantioselectivity.