Release Time:2019-03-09  Hits:

Indexed by: Journal Article

Date of Publication: 2014-09-01

Journal: SYNLETT

Included Journals: Scopus、SCIE

Volume: 25

Issue: 15

Page Number: 2155-2160

ISSN: 0936-5214

Key Words: cinchona alkaloid; organocatalysis; enantioselectivity; beta-keto esters; industrial application

Abstract: A highly efficient alpha-hydroxylation of beta-keto esters catalyzed by cupreidine in the presence of cumyl hydroperoxide (CHP) was achieved. The reaction was applied to a wide variety of beta-keto esters to give products in high yields (up to 95%) with excellent enantioselectivities (up to 97% ee). The reaction had been successfully scaled up to a gram quantity and (S)-5-chloro-2-hydroxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate - the important intermediate of Indoxacarb were obtained in 96% yield with 86% ee. The enantiomeric excess could be improved to 99% by crystallization, and this method has prospect of industrial application for its advantages of enantioselectivity, ease of catalyst preparation and reclamation of catalyst.