An intramolecular stereospecific reductive cross-electrophile coupling reaction of 2-aryl-4-chlorotetrahydropyrans has been developed. These substrates undergo a nickel-catalyzed ring contraction to afford disubstituted cyclopropanes with excellent stereochemical fidelity at both the alkyl halide and ether bearing stereogenic centers. This new method provides access to stereochemically defined cyclopropanes in two steps from commercially available aldehydes.

Cyclopropane synthesis via stereospecific intramolecular reductive cross-electrophile couplings

251st National Meeting (2016)

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