American Chemical Society
ol8b03973_si_001.pdf (7.31 MB)

Synthesis of 2‑(2-Oxo-2-phenyl­ethyl)­cyclo­pentanone by Rhodium-Catalyzed Tandem Alkynyl Cyclobutanols Hydroacylation and Semipinacol Rearrangement

Download (7.31 MB)
journal contribution
posted on 2019-02-12, 19:19 authored by Rui Guo, Xueling Mo, Guozhu Zhang
A rhodium-catalyzed tandem reaction of alkynyl cyclobutanols with salicylaldehydes has been developed. The reaction offers a new and atom-economical approach for the selective preparation of multisubstituted 2-(2-oxo-2-phenylethyl)­cyclo­pentanone in high yields under mild reaction conditions with tolerance of a broad range of substituted alkynyl cyclobutanols and salicylaldehyes. The isolation of intermediate suggests that the reaction proceeds through a sequential process of intermolecular hydroacylation and semipinacol rearrangement.