Kinetic Resolution of Oxaziridines via Chiral Bifunctional Guanidine-Catalyzed Enantioselective α‑Hydroxylation of β‑Keto Esters

An efficient kinetic resolution of racemic oxaziridines has been realized via catalytic asymmetric α-hydroxylation of available β-keto esters. In the presence of a chiral bifunctional guanidine catalyst, a variety of optically active oxaziridines and chiral α-hydroxy β-keto esters were generated wit...

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Bibliographic Details
Published in:Organic letters 2016-08, Vol.18 (15), p.3602-3605
Main Authors: Lin, Xiaobin, Ruan, Sai, Yao, Qian, Yin, Chengkai, Lin, Lili, Feng, Xiaoming, Liu, Xiaohua
Format: Article
Language:English
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Summary:An efficient kinetic resolution of racemic oxaziridines has been realized via catalytic asymmetric α-hydroxylation of available β-keto esters. In the presence of a chiral bifunctional guanidine catalyst, a variety of optically active oxaziridines and chiral α-hydroxy β-keto esters were generated with excellent results (ee’s of up to 99% and 97% and yields of up to 44% and 54%, respectively).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01614