Axially chiral macrocyclic -alkene bearing bisazole component formed by sequential C-H homocoupling and ring-closing metathesis

西尾 正太郎*; 染手 隆司*; 杉江 敦司*; 小林 徹; 矢板 毅; 森 敦紀*

Organic Letters, 14(10), p.2476 - 2479, 2012/05

https://doi.org/10.1021/ol300755y

Clipping by ring-closing metathesis freezes rotation of a C-C bond to result in forming axial chirality. Treatment of bisbenzimidazole bearing an -(3-butenyl) substituent with a Grubbs' catalyst undergoes ring-closing metathesis, in which the stereochemistry of the thus formed olefin was exclusively -form. Analysis by HPLC with a chiral stationary column confirmed clear baseline separation of each enantiomer.