Unmasking the 6,7,5-tricarbocyclic frame of

JR Rodriguez; L Castedo; JL Mascarenas

doi:10.1021/jo9917893

Unmasking the 6,7,5-tricarbocyclic frame of

J Org Chem. 2000 Apr 21;65(8):2528-31. doi: 10.1021/jo9917893.

Authors

JR Rodriguez¹, L Castedo, JL Mascarenas

Affiliation

¹ Departamento de Quimica Organica, Universidad de Santiago de Compostela, Spain.

PMID: 10789466
DOI: 10.1021/jo9917893

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.