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Asymmetric Ring Opening/Cyclization/Retro‐Mannich Reaction of Cyclopropyl Ketones with Aryl 1,2‐Diamines for the Synthesis of Benzimidazole Derivatives
Author(s) -
Xia Yong,
Lin Lili,
Chang Fenzhen,
Liao Yuting,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2016
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.201604735
Subject(s) - benzimidazole , cycloheptene , chemistry , ring (chemistry) , mannich reaction , aryl , catalysis , yield (engineering) , amide , combinatorial chemistry , medicinal chemistry , organic chemistry , materials science , alkyl , metallurgy
A highly efficient asymmetric ring‐opening/cyclization/retro‐Mannich reaction of cyclopropyl ketones with aryl 1,2‐diamines has been realized using a chiral N , N′ ‐dioxide/Sc III catalyst. Benzimidazoles containing chiral side chains were generated under mild reaction conditions in excellent outcomes (up to 99 % yield and 97 % ee ). This method also provides efficient access to chiral benzimidazole‐substituted amide and cycloheptene derivatives.