Accessing Cyclopentenones via Intramolecular Rhodium-Catalyzed Hydroacylation of Alkynyl Aldehydes

Keywords

rhodium catalysis - hydroacylation - cyclopentenone

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