Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 69, Issue 5, Pages 1557-1564Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0352732
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The reaction of alkenes with conjugated ene-yne-ketones, such as 1-benzoyl-2-ethynyleycloalkenes, with a catalytic amount of Cr(CO)(5)(THF) gave 5-phenyl-2-furylcyclopropane derivatives in good yields. The key intermediate of this cyclopropanation is a (2-furyl)carbene complex generated by a nucleophilic attack of carbonyl oxygen to an internal alkyne carbon in pi-alkyne complex or sigma-vinyl cationic complex. A wide range of late transition metal compounds, such as [RuCl2(CO)(3)](2), [RhCl-(cod)12, [Rh(OAc)(2)](2), PdCl2, and PtCl2, also catalyzes the cyclopropanation of alkenes with ene-yne-ketones effectively. When the reactions were carried out with dienes as a carbene acceptor, the more substituted or more electron-rich alkene moiety was selectively cyclopropanated with the (2-furyl)carbenoid intermediate.
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