Journal
TETRAHEDRON
Volume 66, Issue 51, Pages 9708-9713Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.10.032
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Funding
- National Natural Science Foundation of China [20973051]
- Zhejiang Provincial Natural Science Foundation of China [Y4090139]
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The highly enantioselective synthesis of warfarin and its analogs was reported in this manuscript And a cooperative catalysis was observed in asymmetric primary amine-catalyzed Michael reaction for the enantioselective synthesis of warfarin and its analogs, which led to the finding of several cooperative catalyst systems combined with Lewis acid and primary amine, such as LiClO4/DPEN. In this Michael reaction of 4-hydrocoumarin, the cooperative catalyst system (LiClO4/DPEN) resulted in higher levels of stereoselectivity (up to 94%ee). Additionally, the mechanism of the enantioselectivity enhancement in the cooperative catalytic Michael reaction has been investigated by using of ESI-MS and the study of nonlinear effect. (C) 2010 Elsevier Ltd. All rights reserved.
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