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Asymmetric Synthesis of 2,3‐Dihydropyrroles by Ring‐Opening/Cyclization of Cyclopropyl Ketones Using Primary Amines
Author(s) -
Xia Yong,
Liu Xiaohua,
Zheng Haifeng,
Lin Lili,
Feng Xiaoming
Publication year - 2015
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.201407880
Subject(s) - kinetic resolution , yield (engineering) , primary (astronomy) , chemistry , nucleophile , amine gas treating , scandium , ring (chemistry) , catalysis , medicinal chemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , physics , thermodynamics , astronomy
The asymmetric ring‐opening/cyclization of cyclopropyl ketones with primary amine nucleophiles was catalyzed by a chiral N , N ′‐dioxide/scandium(III) complex through a kinetic resolution process. A broad range of cyclopropyl ketones and primary amines are suitable substrates of this reaction. The corresponding products were afforded in excellent enantioselectivities and yields (up to 97 % ee and 98 % yield) under mild reaction conditions. This method provides a promising access to chiral 2,3‐dihydropyrroles as well as an effective procedure for the kinetic resolution of 2‐substituted cyclopropyl ketones.