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Asymmetric Reductive and Alkynylative Heck Bicyclization of Enynes to Access Conformationally Restricted Aza[3.1.0]bicycles

Xiaolei Huang, Minh Hieu Nguyen, Maoping Pu, Luoqiang Zhang, Yonggui Robin, Yun‐Dong Wu, Jianrong Steve Zhou

2020Angewandte Chemie International Edition31 citationsDOIOpen Access PDF

Abstract

Conformationally restricted azabicycles are becoming increasingly important in medicinal research. Asymmetric Heck bicyclization of enynes proceeds to give medicinally useful aza[3.1.0] and aza[4.1.0] bicycles with excellent enantioselectivity. The key organopalladium species after bicyclization can be trapped by silanes and terminal alkynes.

Topics & Concepts

OrganopalladiumHeck reactionSilanesChemistryCombinatorial chemistryAsymmetric hydrogenationStereochemistryEnantioselective synthesisCatalysisPalladiumOrganic chemistrySilaneCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsCatalytic Alkyne Reactions