Bridgehead vicinal diallylation of norbornene derivatives and extension to propellane derivatives via ring-closing metathesis

Beilstein J Org Chem. 2016 Aug 22:12:1877-1883. doi: 10.3762/bjoc.12.177. eCollection 2016.

Abstract

Here, we report a simple synthetic strategy to the bridgehead vicinal diallylation of norbornene derivatives. These substrates are useful to generate propellanes via ring-closing metathesis. Single-crystal X-ray diffraction analysis of four compounds led to the realization of configurational correction of earlier reported molecules.

Keywords: norbornene; propellane derivatives; ring-closing metathesis; single-crystal X-ray diffraction; vicinal diallylation.