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Unmasking the 6,7,5-tricarbocyclic frame of
Rodriguez1, Castedo, Mascarenas
1Departamento de Quimica Organica, Universidad de Santiago de Compostela, Spain.
The Journal of Organic Chemistry
|May 2, 2000
Abstract:
Opening of the bridging ether of 8-oxabicyclo[3.2.1]oct-6-ene systems 1,7-fused to a five-membered carbocycle that bears a double bond conjugated to that of the oxabicycle can be induced at low temperaure by the addition of an organolithium reagent. If this double bond is unsubstituted, the opening occurs via an anti-1,6-addition pathway, and if substituted it takes place by means of a more classical syn SN2' addition.