Base‐Catalyzed Stereoselective Vinylation of Ketones with Arylacetylenes: A New C(sp 3 )C(sp 2 ) Bond‐Forming Reaction | Zendy

Trofimov Boris A. | Zendy; Schmidt Elena Yu. | Zendy; Ushakov Igor' A. | Zendy; Zoridezhda V. | Zendy; Skital'tseva Elena V. | Zendy; Protsuk Nadezhda I. | Zendy; Mikhaleva Al'bina I. | Zendy

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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.

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