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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.
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.
Publication History
Article published online:
22 April 2025
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