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Catalytic Enantioselective Aza‐pinacol Rearrangement
Author(s) -
Yu Yuanyuan,
Li Jingwen,
Jiang Long,
Zhang JingRen,
Zu Liansuo
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201705539
Subject(s) - enantioselective synthesis , chemistry , indoline , catalysis , combinatorial chemistry , phosphoric acid , pinacol , stereochemistry , organic chemistry
The first catalytic enantioselective asymmetric aza‐pinacol rearrangement is reported. The reactions are catalyzed by a chiral phosphoric acid and proceed via a highly organized transition state involving a cyclic aza‐ ortho ‐xylylene intermediate to afford the indoline structures with good to excellent enantioselectivity. The synthetic utility of this method is demonstrated by the asymmetric synthesis of a key intermediate to the natural product minfiensine and the identification of a chiral lead compound to repress antibiotic resistance.