Issue 63, 2017

Heterogeneous enantioselective synthesis of chromans via the oxa-Michael–Michael cascade reaction synergically catalyzed by grafted chiral bases and inherent hydroxyls on mesoporous silica surface

Abstract

A heterogeneous enantioselective oxa-Michael–Michael reaction for the synthesis of chromans has been developed on a heterogeneous acid–base synergic catalyst with inherent silica as acidic sites and immobilized chiral amines as basic sites. Final products were afforded in selectivity of up to 98% and ee of 97% from 2-nitrovinyl phenol and 3-methyl-2-butenal. The heterogeneous synergistic catalytic mechanism has also been studied.

Graphical abstract: Heterogeneous enantioselective synthesis of chromans via the oxa-Michael–Michael cascade reaction synergically catalyzed by grafted chiral bases and inherent hydroxyls on mesoporous silica surface

Supplementary files

Article information

Article type
Communication
Submitted
08 May 2017
Accepted
13 Jul 2017
First published
13 Jul 2017

Chem. Commun., 2017,53, 8882-8885

Heterogeneous enantioselective synthesis of chromans via the oxa-Michael–Michael cascade reaction synergically catalyzed by grafted chiral bases and inherent hydroxyls on mesoporous silica surface

S. Wang, J. He and Z. An, Chem. Commun., 2017, 53, 8882 DOI: 10.1039/C7CC03556J

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