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  • Ring-opening metathesis/oxy-cope rearrangement: a new strategy for the synthesis of bicyclic medium ring-containing compounds.

Ring-opening metathesis/oxy-cope rearrangement: a new strategy for the synthesis of bicyclic medium ring-containing compounds.

Journal of the American Chemical Society (2003-12-04)
Brian H White, Marc L Snapper
摘要

Ring-opening/ring-closing metathesis on cyclobutene-containing substrates with angular oxygen functionality provides a stereospecific introduction of 1,5-bis-dienes required for an anion-accelerated oxy-Cope rearrangement. The reaction sequence offers generally a stereocontrolled preparation of a variety of medium ring-containing bicyclic ring systems, while rearrangement to the bicyclo[7,3,0]dodecane (9-5) system leads to a mixture of olefin isomers.

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Sigma-Aldrich
Hoveyda-Grubbs Catalyst® M720, Umicore, 97%