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

• Sambasivarao Kotha and
• Rama Gunta

Beilstein J. Org. Chem. 2016, 12, 1877–1883, doi:10.3762/bjoc.12.177

• Sambasivarao Kotha Rama Gunta Department of Chemistry, Indian Institute of Technology-Bombay, Powai, Mumbai, India 10.3762/bjoc.12.177 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; Introduction The norbornene moiety is a useful template and also a versatile synthon in organic synthesis [1]. The double bond present in the norbornene frame is strained and therefore participates in cycloaddition sequences as a C2-synthon [2][3]. It was reported that the norbornene system is