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Construction of Tropane Derivatives by the Organocatalytic Asymmetric Dearomatization of Isoquinolines
Author(s) -
Xu JinHui,
Zheng ShengCai,
Zhang JiWei,
Liu XinYuan,
Tan Bin
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.201605736
Subject(s) - tropane , stereocenter , enantioselective synthesis , chemistry , stereoselectivity , organocatalysis , mannich reaction , combinatorial chemistry , stereochemistry , catalysis , organic chemistry
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.