Treatment of �-diketones with bis(iodomethyl)zinc results in the formation of a chain-extended cyclopropanol.  Amino acid-based  starting materials can be used to effect stereoselective formation of cyclopropanols. While subsequent cyclopropanol rearrangements are observed with aromatic and aliphatic derived systems, amino acid-based cyclopropanols do not rearrange with the same facility.  The amino acid substituent appears to play a role in the mechanism and in the stereocontrol of cyclopropanol formation.  In addition to synthetic efforts, computational studies using DFT methods provide insight into the formation and rearrangement of systems that may have use as peptidomimetics.

Zinc carbenoid-mediated chain extension of amino acid-derived β-diketones

245th National Meeting (2013)

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