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- Title
Asymmetric Ring Opening/Cyclization/Retro-Mannich Reaction of Cyclopropyl Ketones with Aryl 1,2-Diamines for the Synthesis of Benzimidazole Derivatives.
- Authors
Xia, Yong; Lin, Lili; Chang, Fenzhen; Liao, Yuting; Liu, Xiaohua; Feng, Xiaoming
- Abstract
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/ScIII 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.
- Subjects
KETONES; BENZIMIDAZOLE derivatives; RING formation (Chemistry); MANNICH reaction; CATALYSTS; CYCLOHEPTENE
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 40, p12416
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201604735