The transition metal catalyzed C–C bond activation of strained ring systems constitutes an elegant method for constructing new carbon-carbon or carbon-heteroatom bonds. Although a number of small rings have been successfully exploited in metal-catalyzed transformations via this approach, the C–C activation of cyclopropanone derivatives remains underexplored. The challenge arises from the need of a viable precursor that can readily equilibrate to cyclopropanone in mild conditions. Herein, we report a nickel-catalyzed formal [3+2] cycloaddition of cyclopropanone equivalents and internal alkynes, leading to a variety of 2,3-disubstituted cyclopentenones. Notably, the products formed are analogous to the ones obtained in the classical Pauson-Khand reaction, but with reverse regiocontrol.

Synthesis of cyclopentenones via Ni-catalyzed formal [3+2] cycloaddition of cyclopropanones and internal alkynes

2019 Fall National Meeting

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