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Organocatalytic Enantioselective α‐Amination by Conjugate Addition of 5 H ‐Thiazol‐4‐ones to Arylazocarboxylates: Access to Chiral N , S ‐acetals
Author(s) -
Lin Xiao,
Fang Fang,
Lin Wei,
Liu Zhantao,
Chang Xiaoyong,
Li Pengfei,
Li Wenjun
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000355
Subject(s) - chemistry , enantioselective synthesis , conjugate , amination , phosphoric acid , michael reaction , organocatalysis , catalysis , adduct , acetal , stereoselectivity , stereochemistry , optically active , combinatorial chemistry , organic chemistry , mathematical analysis , mathematics
A chiral phosphoric acid catalyzed stereoselective Michael addition of 5 H ‐thiazol‐4‐ones to arylazocarboxylates was developed for the construction of optically active N , S ‐acetal frameworks. Both 1‐naphthylazocarboxylates and phenylazocarboxylates were compatible to afford a series of 1,4‐adducts in generally high yields and enantioselectivities. Notably, the catalytic protocol enables the formation of N , S ‐acetals featuring thiazol‐4‐one skeleton.