Literature DB >> 28388053

Catalytic Enantioselective Synthesis of 3,4-Unsubstituted Thiochromenes through Sulfa-Michael/Julia-Kocienski Olefination Cascade Reaction.

Amit Kumar Simlandy1, Santanu Mukherjee1.   

Abstract

A highly enantioselective cascade sulfa-Michael/Julia-Kocienski olefination reaction between 2-mercaptobenzaldehydes and β-substituted vinyl PT-sulfones has been realized for the synthesis of 3,4-unsubstituted 2H-thiochromenes. This reaction, catalyzed by diphenylprolinol TMS ether, proceeds through an aromatic iminium intermediate and furnishes a wide range of 2-substiuted 2H-thiochromenes with excellent enantioselectivities (up to 99:1 er).

Entities:  

Year:  2017        PMID： 28388053     DOI： 10.1021/acs.joc.7b00579

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  2 in total

1.  Bifunctional iminophosphorane catalysed enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles.

Authors:  Michele Formica; Geoffroy Sorin; Alistair J M Farley; Jesús Díaz; Robert S Paton; Darren J Dixon
Journal:  Chem Sci       Date:  2018-07-23       Impact factor: 9.825

2.  Crystal structures of 2-(2-bromo-5-fluoro-phen-yl)-8-eth-oxy-3-nitro-2H-thio-chromene and 2-(2-bromo-5-fluoro-phen-yl)-7-meth-oxy-3-nitro-2H-thio-chromene.

Authors:  Chien Thang Pham; Dinh Hung Mac; Thai Thanh Thu Bui
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2019-10-31
  2 in total

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