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. 2012 Mar 16;14(6):1584-7.
doi: 10.1021/ol300330t. Epub 2012 Mar 2.

Rhodium-catalyzed carbonylation of 3-acyloxy-1,4-enynes for the synthesis of cyclopentenones

Xiaoxun Li  1 , Suyu Huang, Casi M Schienebeck, Dongxu Shu, Weiping Tang
Affiliations

Rhodium-catalyzed carbonylation of 3-acyloxy-1,4-enynes for the synthesis of cyclopentenones

Xiaoxun Li et al. Org Lett. .

Abstract

Functionalized cyclopentenones were synthesized by a Rh-catalyzed carbonylation of 3-acyloxy-1,4-enynes, derived from alkynes and α,β-unsaturated aldehydes. The reaction involved a Saucy-Marbet 1,3-acyloxy migration of propargyl esters and a [4 + 1] cycloaddition of the resulting acyloxy substituted vinylallene with CO.

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Figures

Scheme 1
Scheme 1
Carbonylation of 3-acyloxy-1,4-enyne for the synthesis of cyclopentenones
Scheme 2
Scheme 2
Carbonylation of 3-acyloxy-1,4-enyne with di- and trisubstituted alkenes
Scheme 3
Scheme 3
Functionalization of cyclpentenones derived carbonylation of 3-acyloxy-1,4-enynes
Scheme 4
Scheme 4
Proposed mechamism for the carbonylation of 3-acyloxy-1,4-enynes
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