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Published on: May 26, 2019
Copper-Catalyzed SN2'-Type Allylic Substitution of gem-Dichlorocyclobutenones with Cyclopropanols
Min-Min Liu1, Xiao-Die An1, Jun-Fei Wang1
1State Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, 1200 Cailun Road, Shanghai201203, China.
Abstract:
Both gem-dichlorocyclobutenones and cyclopropanols are versatile building blocks in organic synthesis. Herein, we report a Cu/dppp-catalyzed SN2'-type allylic substitution of gem-dichlorocyclobutenones with cyclopropanols. The reaction proceeds smoothly via a copper homoenolate intermediate under mild conditions and exhibits a broad substrate scope, affording densely functionalized cyclobutenones with high efficiency. Moreover, a scale-up experiment and several product derivatizations were conducted to showcase the synthetic utility of this method.
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