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. 2005 Sep 14;127(36):12440-1.
doi: 10.1021/ja0529687.

Iodomethylzinc phosphates: powerful reagents for the cyclopropanation of alkenes

Marie-Christine Lacasse  1 , Cyril Poulard, André B Charette
Affiliations

Iodomethylzinc phosphates: powerful reagents for the cyclopropanation of alkenes

Marie-Christine Lacasse et al. J Am Chem Soc. .

Abstract

A new family of zinc carbenoids derived from phosphoric acids was developed and used in the cyclopropanation of allylic alcohols and ethers and also of unfunctionalized olefins. The use of the chiral phosphoric acid of a 3,3'-disubstituted BINOL leads to efficient stereocontrol, affording the cyclopropanes of allylic and homoallylic ethers with complete conversions and up to 93% ee. A catalytic version of this reaction using 10 mol % of the chiral phosphate reagent is also disclosed.

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