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Brønsted Base Catalyzed Conjugate Addition of β-Acylvinyl Anion Equivalents to α,β-Unsaturated Ketones

Authors :
Masahiro Terada
Azusa Kondoh
Sho Yamaguchi
Yushi Watanabe
Source :
Synlett. 33:1853-1857
Publication Year :
2022
Publisher :
Georg Thieme Verlag KG, 2022.

Abstract

A Brønsted base catalyzed addition reaction of allyl sulfones having a diethoxyphosphoryloxy group, which are new precursors of β-acylvinyl anion equivalents, with α,β-unsaturated ketones was developed. The reaction proceeded efficiently under the influence of a phosphazene base as the catalyst. This is a rare example of a catalytic addition reaction of β-acylvinyl anion equivalents. A preliminary study on an asymmetric variant was also conducted with a chiral bis(guanidino)iminophosphorane catalyst.

Subjects

Subjects :
Organic Chemistry

Details

ISSN :
14372096 and 09365214
Volume :
33
Database :
OpenAIRE
Journal :
Synlett
Accession number :
edsair.doi...........357b2372bc5a5b53d42a33167925fb58
Full Text :
https://doi.org/10.1055/a-1827-5652