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Indexed by:期刊论文

Date of Publication:2012-09-23

Journal:TETRAHEDRON

Included Journals:SCIE、Scopus

Volume:68

Issue:38

Page Number:7973-7977

ISSN No.:0040-4020

Key Words:Chiral drug; Aryloxy aminopropanol organocatalyst; beta-Keto ester; Asymmetric alpha-hydroxylation

Abstract:A screen of aryloxy aminopropanol organocatalysts derived from the beta-blocker inhibitor S-timolol determined the most active catalyst of asymmetric alpha-hydroxylation of beta-keto esters. (R)-1-(tert-butylamino)-3-(3,4,5-trimethoxyphenoxy) propan-2-ol (3k) was the most effective derivative, enantioselectively catalyzing alpha-hydroxylation of beta-keto esters using tert-butyl hydroperoxide as the oxidant in hexane to afford the corresponding products in excellent yield and with good enantioselectivity (up to 96% yield, 88% ee). (C) 2012 Elsevier Ltd. All rights reserved.