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Indexed by:期刊论文

Date of Publication:2010-12-01

Journal:EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Included Journals:SCIE、Scopus

Issue:34

Page Number:6525-6530

ISSN No.: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.