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Chiral Phosphoric Acid Catalyzed Asymmetric Ugi Reaction by Dynamic Kinetic Resolution of the Primary Multicomponent Adduct
Author(s) -
Zhang Yun,
Ao YuFei,
Huang ZhiTang,
Wang DeXian,
Wang MeiXiang,
Zhu Jieping
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201600751
Subject(s) - kinetic resolution , chemistry , adduct , ugi reaction , enantioselective synthesis , catalysis , primary (astronomy) , phosphoric acid , organocatalysis , combinatorial chemistry , organic chemistry , stereochemistry , isocyanide , physics , astronomy
Reaction of isonitriles with 3‐(arylamino)isobenzofuran‐1(3 H )‐ones in the presence of a catalytic amount of an octahydro ( R )‐binol‐derived chiral phosphoric acid afforded 3‐oxo‐2‐arylisoindoline‐1‐carboxamides in high yields with good to high enantioselectivities. An enantioselective Ugi four‐center three‐component reaction of 2‐formylbenzoic acids, anilines, and isonitriles was subsequently developed for the synthesis of the same heterocycle. Mechanistic studies indicate that the enantioselectivity results from the dynamic kinetic resolution of the primary Ugi adduct, rather than from the C−C bond‐forming process. The resulting heterocycle products are of significant medicinal importance.