Catalytic Enantioselective de novo Construction of Chiral Arenes through Desymmetrizing Oxidative 4+2-Cycloaddition

Ghosh, B and Harariya, MS and Mukherjee, S (2022) Catalytic Enantioselective de novo Construction of Chiral Arenes through Desymmetrizing Oxidative 4+2-Cycloaddition. In: Angewandte Chemie - International Edition .

PDF ang_che_2022.pdf - Published Version Restricted to Registered users only Download (13MB) | Request a copy

Abstract

Central chirality in arene derivatives arising out of unsymmetrically substituted arene ring is a fascinating yet rarely explored research topic. Here, we report a desymmetrization approach to centrally chiral unfunctionalized arenes, which is enabled by the enantioselective de novo construction of the arene ring. This operationally simple protocol is based on a [4+2]-cycloaddition between polycyclic meso-cyclohexenediones and α,β-unsaturated aldehydes, and doesn't usually require any external oxidant. Catalyzed by a diphenylprolinol silyl ether, this reaction proceeds via dienamine intermediate and greatly simplifies the access to diversely substituted chiral arenes with outstanding enantioselectivities.

Item Type:	Journal Article
Publication:	Angewandte Chemie - International Edition
Publisher:	John Wiley and Sons Inc
Additional Information:	The copyright for this article belongs to the John Wiley and Sons Inc.
Keywords:	Aromatic hydrocarbons; Enantioselectivity; Reaction intermediates, Arene derivatives; Arene rings; Chiral arene; Desym-metrization; Dienamine; Dienamine catalyse; Enantioselective; Organocatalysis; 4 + 2 cycloaddition; 4+2-cycloaddition, Catalysis
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	23 Aug 2022 05:28
Last Modified:	23 Aug 2022 05:28
URI:	https://eprints.iisc.ac.in/id/eprint/76165

Actions (login required)

View Item