Rhodium-Catalyzed Carbonylation of 3-Acyloxy-1,4-enynes for the Synthesis of Cyclopentenones

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...

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Bibliographic Details
Published in:Organic letters 2012-03, Vol.14 (6), p.1584-1587
Main Authors: Li, Xiaoxun, Huang, Suyu, Schienebeck, Casi M, Shu, Dongxu, Tang, Weiping
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Catalysis
Combinatorial Chemistry Techniques
Cyclization
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Molecular Structure
Rhodium - chemistry
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300330t