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Synlett 1995; 1995(12): 1197-1207
DOI: 10.1055/s-1995-5231
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The Asymmetric Cyclopropanation of Acyclic Allylic Alcohols: Efficient Stereocontrol with Iodomethylzinc Reagents

André B. Charette* , Jean-François Marcoux
  • *Département de Chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7, Fax (514) 343-5900; e-mail: charetta@ERE.UMontreal.CA
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Publication Date:
31 December 2000 (online)

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The asymmetric cyclopropanation of acyclic allylic alcohols can now be achieved with unprecedently high level of stereocontrol with halomethylzinc reagents. The ability of proximal basic groups to ”deliver” the methylene unit to a nearby olefin has been used to develop efficient reaction conditions for the cyclopropanation of allylic alcohols. This property was employed to improve the diastereoselection observed in the cyclopropanation of chiral, acyclic allylic alcohols; in the development of an efficient chiral auxiliary; and finally in the design of an efficient stoichiometric chiral reagent for the cyclopropanation of allylic alcohols.

cyclopropanation - chiral auxiliaries - organozinc - carbenoids - allylic alcohols