Litcius/Paper detail

Catalytic Desymmetric Dicarbofunctionalization of Unactivated Alkenes

Xianqing Wu, Baixue Luan, Wenyu Zhao, Feng He, Xin‐Yan Wu, Jingping Qü, Yifeng Chen

2022Angewandte Chemie International Edition61 citationsDOI

Abstract

The construction of multi-stereocenters by a transition metal-catalyzed cross-coupling reaction is a major challenge. The catalytic desymmetric functionalization of unactivated alkenes remains largely unexplored. Herein, we disclose -a desymmetric dicarbofunctionalization of 1,6-dienes via a nickel-catalyzed reductive cross-coupling reaction. The leverage of the underdeveloped chiral 8-Quinox enables the Ni-catalyzed desymmetric carbamoylalkylation of both unactivated mono- and disubstituted alkenes to form pyrrolidinone bearing two nonadjacent stereogenic centers in high enantio- and stereoselectivitives with broad functional-group tolerance. The synthetic application of pyrrolidinones allows the rapid access to complex chiral fused-heterocycles.

Topics & Concepts

StereocenterCatalysisChemistryPyrrolidinonesCombinatorial chemistryFunctional groupSurface modificationNickelCoupling reactionEnantioselective synthesisStereochemistryOrganic chemistryPhysical chemistryPolymerAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis