The Asymmetric Cyclopropanation of Acyclic Allylic Alcohols: Efficient Stereocontrol with Iodomethylzinc Reagents

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Abstract
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.

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