A novel class of tunable cyclopropanation reagents (RXZnCH2Y) and their synthetic applications.

The Simmons-Smith cyclopropanation is a widely used method to synthesize cyclopropanes from alkenes using methylene iodide and a zinc reagent. A novel class of organozinc species, RXZnCH(2)Y, has been found to efficiently cyclopropanate alkenes, including traditionally unreactive unfunctionalized alkenes. The reactivity and selectivity of this class of organozinc reagents can be regulated by tuning the electronic and/or steric nature of the RX group attached to Zn. During recent years, this class of organozinc reagent has been widely used in organic synthesis as a reagent for cyclopropanation and other useful synthetic transformations. Catalytic, asymmetric versions of this reaction have been developed providing high enantiomeric excess for unfunctionalized olefins.