We investigated the enantioselective Simmons-Smith cyclopropanation using substituted zinc carbenoids and a dioxaborolane-derived chiral ligand to gain access to 1,2,3-trisubstituted cyclopropanes in enantioenriched form. The stereoselective iodocyclopropanation of allylic alcohols was achieved using iodoform as the carbenoid precursor and the resulting cyclopropanes were functionalized into a variety of 1,2,3-trisubstituted cyclopropanes. The homologous stereoselective chlorocyclopropanation reaction was carried out using chlorodiiodomethane as the zinc carbenoid precursor.

Highly enantioselective synthesis of 1,2,3-substituted cyclopropanes using α-iodozinc and α-chlorozinc carbenoids

243rd National Meeting (2012)

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