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

Org Lett. 2012 May 18;14(10):2476-9. doi: 10.1021/ol300755y. Epub 2012 May 2.

Abstract

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.