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Base‐Catalyzed Stereoselective Vinylation of Ketones with Arylacetylenes: A New C(sp 3 )C(sp 2 ) Bond‐Forming Reaction
Author(s) -
Trofimov Boris A.,
Schmidt Elena Yu.,
Ushakov Igor' A.,
Zoridezhda V.,
Skital'tseva Elena V.,
Protsuk Nadezhda I.,
Mikhaleva Al'bina I.
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000227
Subject(s) - stereoselectivity , chemistry , catalysis , base (topology) , medicinal chemistry , stereochemistry , organic chemistry , mathematical analysis , mathematics
Alkylaryl‐ and alkylheteroarylketones, including those with condensed aromatic moieties, are readily vinylated with arylacetylenes (KOH/DMSO, 100 °C, 1 h) to give regio‐ and stereoselectively the ( E ) ‐ β‐γ‐ethylenic ketones (( E )‐3‐buten‐1‐ones) in 61–84 % yields and with approximately 100 % stereoselectivity. This vinylation represents a new C(sp 3 )C(sp 2 ) bond‐forming reaction of high synthetic potential.