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Target Specific Tactics in Olefin Metathesis: Synthetic Approach to cis-syn-cis-Triquinanes and -Propellanes
Sambasivarao Kotha1, Vikas R Aswar1
1Department of Chemistry, Indian Institute of Technology Bombay Powai , Mumbai, 400 076, India.
Abstract:
A concise and simple synthetic approach to cis-syn-cis-triquinanes and -propellanes has been demonstrated via olefin metathesis starting with exo-nadic anhydride. This approach involves a ring-opening and ring-closing metathesis sequence of norbornene derivatives using Grubb's catalyst. Early-stage diallylation of norbornene derivatives is demonstrated followed by ring-closing metathesis that delivers propellanes exclusively. Surprisingly, ring-opening metathesis, late-stage diallylation, followed by ring-closing metathesis delivers triquinane as well as propellane derivatives.
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