Wednesday, October 23, 2013

Transfer of Chirality in the Rhodium-Catalyzed Intramolecular [5+2] Cycloaddition of 3-Acyloxy-1,4-enynes (ACEs) and Alkynes: Synthesis of Enantioenriched Bicyclo[5.3.0]decatrienes

by Xing-zhong Shu, Casi M. Schienebeck, Wangze Song, Ilia A. Guzei, Weiping Tang*



Thumbnail image of graphical abstract


Chiral bicycles: Enantioenriched bicyclo[5.3.0]decatrienes were prepared from readily available chiral 3-acyloxy-1,4-enynes (ACEs) for the first time. In most cases, the chirality of the ACEs could be transferred to the bicyclic products with high efficiency. Inversion of the configuration was observed, thus confirming the predictions of previous computational studies.

Angewandte Chemie International Edition
Article first published online: 21 OCT 2013



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