Catalytic Asymmetric Conjugate Addition of Tritylthiol to Azadienes with a Bifunctional Organocatalyst

A highly enantioselective sulfa-Michael addition of tritylthiol to azadienes catalyzed by a bifunctional squaramide organocatalyst is described, giving the chiral aminothioethers bearing benzofuran motif with high yields and up to 94% of enantioselectivity. Notably, the aromatization to form the ben...

Full description

Saved in:
Bibliographic Details
Published inAsian journal of organic chemistry Vol. 7; no. 8; pp. 1561 - 1564
Main Authors Gu, Zheng, Xie, Jiao-Jiao, Jiang, Guo-Fang, Zhou, Yong-Gui
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.08.2018
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
enantioselectivity
sulfa-Michael addition
3 CONTIGUOUS STEREOCENTERS
NONCOVALENT ORGANOCATALYST
N-HETEROCYCLIC CARBENE
ENANTIOSELECTIVE SYNTHESIS
ALDOL REACTIONS
BOND FORMATION
ALPHA
organocatalysis
azadienes
ALKYL THIOLS
CONSTRUCTION
thiols
Online AccessGet more information

Cover

More Information
Summary:A highly enantioselective sulfa-Michael addition of tritylthiol to azadienes catalyzed by a bifunctional squaramide organocatalyst is described, giving the chiral aminothioethers bearing benzofuran motif with high yields and up to 94% of enantioselectivity. Notably, the aromatization to form the benzofuran is the driving force.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201800299