Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
Org Biomol Chem. 2012 Aug 7;10(29):5498-513. doi: 10.1039/c2ob25481f. Epub 2012 Jun 12.
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.
西蒙斯-史密斯环丙烷化反应是一种广泛应用的方法，可使用亚甲基碘和锌试剂将烯烃转化为环丙烷。人们发现一类新型有机锌物种 RXZnCH(2)Y 可以有效地将烯烃环丙烷化，包括传统上不易反应的无官能团烯烃。通过调节与 Zn 相连的 RX 基团的电子和/或空间性质，可以调节这类有机锌试剂的反应性和选择性。近年来，这类有机锌试剂已广泛应用于有机合成中，作为环丙烷化和其他有用的合成转化的试剂。该反应的催化、对映选择性版本已经被开发出来，为无官能团烯烃提供了高对映过量。
