Silver‐Catalyzed Asymmetric Double Desymmetrization via Vinylogous Michael Addition of Prochiral α,α‐Dicyanoalkenes to Cyclopentendiones

Author:

Choudhary Kavita1ORCID,Joshi Harshit1,Rohilla Shweta1,Singh Vinod K.1ORCID

Affiliation:

1. Department of Chemistry Indian Institute of Technology Kanpur Kanpur 208016 Uttar Pradesh India) .

Abstract

AbstractAn asymmetric double desymmetrization methodology has been developed for synthesizing densely functionalized chiral cyclopentylcyclohexane scaffolds. We have constructed four chiral centers, including an all‐carbon quaternary stereocenter in a single C−C bond formation event. The methodology has high functional‐group tolerance and delivers a broad range of enantioenriched products. This vinylogous Michael addition reaction of prochiral α,α‐dicyanocyclohexane to 2,2‐disubstituted cyclopentene‐1,3‐dione is catalyzed by a chiral Ag‐(R)‐DTBM‐SEGPHOS catalyst.

Funder

Science and Engineering Research Board

Publisher

Wiley

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