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Transition Metal‐Free Stereoselective α‐Vinylation of Cyclic Ketones with Arylacetylenes in the Superbasic Catalytic Triad Potassium Hydroxide/ tert ‐Butyl Alcohol/Dimethyl Sulfoxide
Author(s) -
Trofimov Boris A.,
Schmidt Elena Yu.,
Zoridezhda V.,
Ivanova Elena V.,
Ushakov Igor' A.,
Mikhaleva Al'bina I.
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200210
Subject(s) - chemistry , potassium hydroxide , catalysis , alcohol , medicinal chemistry , dimethyl sulfoxide , stereoselectivity , transition metal , sulfoxide , triad (sociology) , yield (engineering) , potassium , alcohol oxidation , organic chemistry , psychology , materials science , psychoanalysis , metallurgy
A stereoselective α‐vinylation of cycloaliphatic ketones with arylacetylenes under the transition metal‐free conditions has been developed. The reaction is promoted by the superbasic catalytic triad potassium hydroxide/ tert ‐butyl alcohol/dimethyl sulfoxide (80–110 °C, 1–2 h) to afford mainly ( E )‐β,γ‐ethylenic ketones, their ( E )‐α,β‐isomers being minor products, in up to 83% total yield.