The Nickel-catalyzed stereospecific reductive cross-electrophile coupling reaction of 2-aryl and 2-allylic tetrahydropyrans, with various halogen groups at the C4 position, to form cyclopropanes has been investigated. Benzylic THPS produce cyclopropanes in good yields and high stereospecificity relative to both the alkyl halide and benzylic ether stereocenters. Allylic THPs proceed with moderate yields and stereospecificty utilizing several different halogen leaving groups.  Both methods provide access to substituted cyclopropanes in two steps from commerically available aldehydes.

Nickel-catalyzed, stereospecific, intramolecular, reductive cross-electrophile coupling of allylic and benzylic ethers with alkyl halides

251st National Meeting (2016)

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