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Chiral Primary Amine Catalyzed Enantioselective Protonation via an Enamine Intermediate
Author(s) -
Fu Niankai,
Zhang Long,
Li Jiuyuan,
Luo Sanzhong,
Cheng JinPei
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201105477
Subject(s) - enamine , protonation , enantioselective synthesis , chemistry , amine gas treating , catalysis , organocatalysis , stereochemistry , combinatorial chemistry , organic chemistry , ion
Enamine protonation : A chiral diamine catalyzes an asymmetric Friedel–Crafts reaction through catalytic enantioselective protonation of an enamine. This process can be applied to a range of α‐substituted acroleins and indoles with high yields of products and high enantioselectivity (up to 94 % ee ). An OH/π interaction between H 2 O and the indole ring was found to play an important role in the transition state (see scheme).