Axially Chiral Macrocyclic E-Alkene Bearing Bisazole Component Formed by Sequential C-H Homocoupling and Ring-Closing Metathesis
Axially Chiral Macrocyclic E-Alkene Bearing Bisazole Component Formed by Sequential C-H Homocoupling and Ring-Closing Metathesis
复制标题
DOI：
10.1021/ol300755y
复制
发表时间：
2012-05-18
期刊：
影响因子：
5.2
通讯作者：
Mori, Atsunori
中科院分区：
文献类型：
--
作者：
Nishio, Shotaro;Somete, Takashi;Mori, Atsunori
通过闭环复分解的剪切冻结C-C键的旋转以导致形成轴向手性。用Grubbs催化剂处理带有N-（3-丁烯基）取代基的双苯并咪唑进行闭环复分解，其中由此形成的烯烃的立体化学仅为E-型。通过使用手性固定柱的HPLC分析证实了每种对映异构体的清晰基线分离。
Clipping by ring-closing metathesis freezes rotation of a C-C bond to result in forming axial chirality. Treatment of bisbenzimidazole bearing an N-(3-butenyl) substituent with a Grubbs' catalyst undergoes ring-closing metathesis, in which the stereochemistry of the thus formed olefin was exclusively E-form. Analysis by HPLC with a chiral stationary column confirmed clear baseline separation of each enantiomer.