Although the Simmons–Smith reaction was first reported over fifty years ago, it remains one of the most relevant methods for cyclopropanation today. Asymmetric variants of the Simmons-Smith are rare and often limited to allylic alcohols as substrates. Additionally, more hindered zinc carbenoids are not well-tolerated in the reaction. Here, we report the use of chiral cobalt complexes as catalysts for enantioselective Simmons–Smith-type reductive cyclopropanations. 2,2-Dichloropropane serves as the methylene source, and Zn is used as a reductant. These catalysts also promote spirocyclopropanations using cyclic <i>gem</i>-dihaloalkanes as carbene precursors.

Asymmetric transition metal catalyzed Simmons–Smith cyclopropanations

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