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DOI: 10.1055/a-2558-1202
Accessing Cyclopentenones via Intramolecular Rhodium-Catalyzed Hydroacylation of Alkynyl Aldehydes
A Versatile New Method for the Synthesis of Cyclopentenones via an Unusual Rhodium-Catalyzed Intramolecular Trans Hydroacylation of an Alkyne.
J. Am. Chem. Soc. 2001;
123: 11492-11493
DOI: 10.1021/ja011907f

Significance
Cyclopentenones are prevalent as either building blocks found in biologically active compounds or are the active core of various natural products. Fu and co-workers utilize an intramolecular hydroacylation of alkyne-tethered aldehydes to afford substituted cyclopentenones in one single step.
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Comment
The authors utilized deuterated substrates at the aldehydic position to probe the mechanism. The resulting cyclopentenone exhibits sole deuterium incorporation at the β-position. Competition studies between deuterated and nondeuterated substrates revealed no crossover occurred and support that the hydroacylation is indeed intramolecular.
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Publication History
Article published online:
22 April 2025
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