期刊
TETRAHEDRON
卷 74, 期 41, 页码 6071-6077出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.08.052
关键词
Acetone; 2-Azido beta-nitrostyrene; 2-Methyltetrahydroquinoline; Michael addition; Reductive cyclization; Thiophosphinamide
资金
- Key laboratory of Elemento-Organic Chemistry
- Collaborative Innovation Center of Chemical Science and Engineering
We have proven that primary amine/thiophosphinamide incorporating (1R,2R)-1,2-diphenylethane-1,2-diamine is an efficient catalyst for the asymmetric Michael addition of acetone to (E)-2-azido beta-nitrostyrenes. Under the optimal reaction conditions, the corresponding Michael addition products were obtained in excellent yields with almost perfect stereocontrol. Upon treatment with Et3SiH/InCl3, the Michael addition products could be successfully converted to the related 2-methyltetrahydroquinolines in acceptable yields with moderate to excellent diastereoselectivity and without appreciable loss in optical purity. This process provides a highly enantioselective pathway for the synthesis of biologically important 2-methyltetrahydroquinoline derivatives. (C) 2018 Elsevier Ltd. All rights reserved.
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