Journal
TETRAHEDRON
Volume 68, Issue 38, Pages 7973-7977Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.07.003
Keywords
Chiral drug; Aryloxy aminopropanol organocatalyst; beta-Keto ester; Asymmetric alpha-hydroxylation
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Funding
- National Natural Science Foundation of China [21176041]
- State Key Laboratory of Fine Chemicals
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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.
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