Synfacts 2025; 21(05): 498
DOI: 10.1055/a-2558-1202
Metals in Synthesis

Accessing Cyclopentenones via Intramolecular Rhodium-Catalyzed Hydroacylation of Alkynyl Aldehydes

Contributor(s):
,
Justin Ching
Tanaka K, Fu GC *. Massachusetts Institute of Technology, Cambridge, USA
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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