Nickel-Catalyzed Enantioselective Synthesis of Cyclobutenes via [2+2] Cycloaddition of α,β-Unsaturated Carbonyls with 1,3-Enynes

Abstract

A Ni(0)/chiral N-heterocyclic carbene (NHC) catalyzed enantioselective and intermolecular [2+2] cycloaddition of α,β-unsaturated carbonyl compounds with conjugated enynes was investigated to produce enantioenriched cyclobutenes (up to 89% ee). The present report reveals the first example of a nickel-catalyzed enantioselective [2+2]-cycloaddition reaction. A newly synthesized imidazolinium salt, L*12·HBF₄, was the most effective NHC precursor for the present catalytic reactions.

Key words

nickel catalysis - N-heterocyclic carbenes - enantioselective - intermolecular - [2+2] cycloaddition - cyclobutenes

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