Transition-metal-free superbase-promoted stereoselective α-vinylation of ketones with arylacetylenes: a general strategy for synthesis of β,γ-unsaturated ketones

Boris A Trofimov; Elena Yu Schmidt; Nadezhda V Zorina; Elena V Ivanova; Igor' A Ushakov

doi:10.1021/jo301005p

Transition-metal-free superbase-promoted stereoselective α-vinylation of ketones with arylacetylenes: a general strategy for synthesis of β,γ-unsaturated ketones

J Org Chem. 2012 Aug 17;77(16):6880-6. doi: 10.1021/jo301005p. Epub 2012 Aug 9.

Authors

Boris A Trofimov¹, Elena Yu Schmidt, Nadezhda V Zorina, Elena V Ivanova, Igor' A Ushakov

Affiliation

¹ A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia. [email protected]

PMID: 22839748
DOI: 10.1021/jo301005p

Abstract

A wide variety of β,γ-unsaturated ketones of E configuration have been obtained in good to excellent yields via KO(t)Bu/DMSO promoted α-vinylation of aliphatic, cycloaliphatic, and alkyl aromatic (heteroaromatic) ketones with diverse arylacetylenes.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Catalysis
Dimethyl Sulfoxide / chemistry
Ketones / chemical synthesis*
Molecular Structure
Stereoisomerism

Substances

Alkynes
Ketones
Dimethyl Sulfoxide