Samarium(II) iodide promoted carbon-carbon bond fragmentation in bicy-clo[2.2.1]heptenes : A facile route to bridged eight membered rings and 1,3-disubstituted cyclopentanes

摘要

Samarium(II) iodide has been found to induce carbon-carbon bond cleavage in a number of bicyclo[2.2.1]heptane de-rivatives having 1,4-dicarbonyl moiety under conditions in which the 1,4=dicarbonyl moiety undergoes intramolecular pina-col coupling. This cleavage reaction offers routes to the synthesis of bridged eight membered rings and 1,3-disubstituted cyclopentanes, important building blocks for natural products synthesis.