Enantioselective Syntheses of 4 H -3,1-Benzoxazines via Catalytic Asymmetric Chlorocyclization of o -Vinylanilides

The catalytic asymmetric halocyclization of alkene is a powerful and straightforward strategy for the synthesis of chiral heterocyclic compounds. Herein, an effective approach to chiral benzoxazine derivatives through organocatalyzed chlorocyclization of -vinylanilides was reported. This method prov...

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Published inJournal of organic chemistry Vol. 85; no. 4; pp. 1882 - 1893
Main Authors Xie, Qinxia, Long, Hai-Jiao, Zhang, Qiong-Yin, Tang, Pei, Deng, Jun
Format Journal Article
LanguageEnglish
Published United States 21.02.2020
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Summary:The catalytic asymmetric halocyclization of alkene is a powerful and straightforward strategy for the synthesis of chiral heterocyclic compounds. Herein, an effective approach to chiral benzoxazine derivatives through organocatalyzed chlorocyclization of -vinylanilides was reported. This method provides facile access to a series of chiral benzoxazines in good to excellent yields (up to 99% yield) and with high-level enantiocontrol (up to 92% ee).
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02395