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- Title
Construction of Tropane Derivatives by the Organocatalytic Asymmetric Dearomatization of Isoquinolines.
- Authors
Xu, Jin-Hui; Zheng, Sheng-Cai; Zhang, Ji-Wei; Liu, Xin-Yuan; Tan, Bin
- Abstract
A chiral-NHC-catalyzed highly diastereo- and enantioselective dearomatizing double Mannich reaction of isoquinolines was developed that provides a powerful and straightforward synthetic route toward substituted tropane derivatives with four contiguous stereocenters. A unique feature of this strategy is the use of readily available isoquinolines to provide two reactive sites for dearomatization, thus opening up an unprecedented approach to tropane derivatives with excellent stereoselectivity. The four-component reactions proceeded smoothly with good results. Thus, the present method is suitable for the diversity-oriented synthesis of useful tropane derivatives with high efficiency.
- Subjects
ENANTIOSELECTIVE catalysis; ISOQUINOLINE; TROPANES; CHEMICAL derivatives; MANNICH reaction
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 39, p11834
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201605736