1.
Org Lett
; 5(20): 3631-4, 2003 Oct 02.
Artigo
em Inglês
| MEDLINE
| ID: mdl-14507190
RESUMO
[reaction: see text] In sharp contrast to their isopropyl counterparts, a variety of (Z)-isopropenyl tertiary bicyclo[2.2.2]octenols undergo facile anionic oxy-Cope rearrangements allowing the stereoselective incorporation of an isopropenyl group into polycyclic skeletons such as the tricyclic system of vinigrol, bicyclo[5.3.1]undecane, and cis-decalin frameworks. This rate acceleration is probably due to the stabilization of the transition state by the additional unsaturation on the terminal position.