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The first enantioselective copper-catalyzed decarboxylative propargylic alkylation has been developed. Treatment of propargyl β-ketoesters with a catalyst, prepared in situ from Cu(CH3 CN)4 BF4 and a newly developed chiral tridentate ketimine P,N,N-ligand under mild reaction conditions, generates β-ethynyl ketones in good yields and with high enantioselectivities without requiring the pregeneration of ketone enolates. This new process provides facile access to a range of chiral β-ethynyl ketones in a highly enantioenriched form.
Zhu et al. (Wed,) studied this question.