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
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.
