Download PDF
Synfacts 2005(3): 0328-0328  
DOI: 10.1055/s-2005-921628
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

New Powerful Reagents for Cyclopropanation of Alkenes

Contributor(s): Paul Knochel, Andrei Gavryushin
M.-C. Lacasse, C. Poulard, A. B. Charette
Université de Montréal, Canada
Further Information

Publication History

Publication Date:
22 November 2005 (online)

    Permissions and Reprints

Significance

Diaryl phosphate was shown to form an adduct with the iodomethylzinc carbenoid [(PhO)2P(O)OCH2ZnI], which may serve as a powerful cyclopropanating reagent for alkenes. It is sufficiently stable for storage and practical to use. The design of a BINOL-based chiral auxiliary led to the compound that can be used in catalytic amounts, offering good yields and enantioselectivities in the cyclopropanation of some allyl ethers.