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Enantioselective Conjugate Addition‐Protonation of 5 H ‐Oxazol‐4‐ones and 5‐Methylene 1,3‐Oxazolidine‐2,4‐diones: 2,2'‐Biphenol‐Induced Diastereoselectivity Switch
Author(s) -
Lu Bohua,
Xin Shuang,
Zhu Bo,
Chang Junbiao
Publication year - 2019
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201900111
Subject(s) - chemistry , protonation , conjugate , enantioselective synthesis , stereocenter , oxazolidine , diastereomer , methylene , stereochemistry , cycloaddition , medicinal chemistry , catalysis , organic chemistry , ion , mathematical analysis , mathematics
Summary of main observation and conclusion A synthetic strategy for catalytic asymmetric conjugate addition‐protonation and diastereoselective switch between 5 H ‐oxazol‐4‐ones and 5‐methylene 1,3‐oxazolidine‐2,4‐diones was established. An array of chiral conjugate addition‐protonation products bearing 1,3‐ O ‐heterotertiary‐ O ‐heteroquarternary nonadjacent stereocenters were obtained in excellent yields, moderate to good diastereoselectivities, and excellent enantioselectivities (up to 97% yield, 11: 1 dr, and 98% ee). Induction by 2,2’‐biphenol could effectively promote the production of the corresponding diastereoisomers via cycloaddition intermedia.