Journal of the American Chemical Society 2003-12-03

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

Brian H White, Marc L Snapper

Index: J. Am. Chem. Soc. 125 , 14901, (2003)

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Abstract

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.