Ring-opening metathesis/oxy-cope rearrangement: a new strategy for the synthesis of bicyclic medium ring-containing compounds.
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.
White
Brian H
BH
Eugene F. Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467, USA.
Snapper
Marc L
ML