Literature DB >> 28737794

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.

Shanshan Wang1, Jing He, Zhe An.   

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.

Entities:  

Year:  2017        PMID: 28737794     DOI: 10.1039/c7cc03556j

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  4 in total

1.  Silica gel-immobilized multidisciplinary materials applicable in stereoselective organocatalysis and HPLC separation.

Authors:  J Tůma; M Kohout
Journal:  RSC Adv       Date:  2018-01-03       Impact factor: 4.036

2.  Diastereoselective synthesis of chroman bearing spirobenzofuranone scaffolds via oxa-Michael/1,6-conjugated addition of para-quinone methides with benzofuranone-type olefins.

Authors:  Hongmei Qin; Qimei Xie; Long He
Journal:  RSC Adv       Date:  2022-06-06       Impact factor: 4.036

3.  Insights into Ag(i)-catalyzed addition reactions of amino alcohols to electron-deficient olefins: competing mechanisms, role of catalyst, and origin of chemoselectivity.

Authors:  Chunhui Liu; Peilin Han; Zhizhong Xie; Zhihong Xu; Donghui Wei
Journal:  RSC Adv       Date:  2018-12-04       Impact factor: 4.036

4.  Enantioselective Michael/Hemiketalization Cascade Reactions between Hydroxymaleimides and 2-Hydroxynitrostyrenes for the Construction of Chiral Chroman-Fused Pyrrolidinediones.

Authors:  Dong-Hua Xie; Cheng Niu; Da-Ming Du
Journal:  Molecules       Date:  2022-08-10       Impact factor: 4.927

  4 in total

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