A novel class of tunable cyclopropanation reagents (RXZnCH2Y) and their synthetic applications
A novel class of tunable cyclopropanation reagents (RXZnCH2Y) and their synthetic applications
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DOI：
10.1039/c2ob25481f
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发表时间：
2012-01-01
影响因子：
3.2
通讯作者：
Shi, Yian
中科院分区：
文献类型：
--
作者：
Cornwall, Richard G.;Wong, O. Andrea;Shi, Yian
simons - smith环丙烷化法是一种广泛使用的用碘化亚甲基和锌试剂从烯烃合成环丙烷的方法。一类新的有机锌化合物RXZnCH2Y被发现能有效地环丙烷化烯烃，包括传统上不反应的非官能化烯烃。这类有机锌试剂的反应性和选择性可以通过调节与锌相连的RX基团的电子和/或空间性质来调节。近年来，这类有机锌试剂作为环丙烷化和其他有用的合成转化试剂被广泛应用于有机合成中。催化，该反应的不对称版本已开发提供高对映体过量的非功能化烯烃。
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, RXZnCH2Y, 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.