85720-11-2Relevant academic research and scientific papers
Electrophile-Initiated Ring-Opening Reactions of 2-Methylene-6,6-dimethylbicyclohexanes. New Methodology for the Synthesis of Highly Functionalized 1,2,3-Trisubstituted Cyclopentenes
Roberts, Richard A.,Schuell, Volker,Paquette, Leo A.
, p. 2076 - 2084 (2007/10/02)
A pair of 1-substituted 2-methylene-6,6-dimethylbicyclohexanes has been determined to undergo smooth cyclopropane ring opening with formation of 1,2,3-trisubstituted cyclopentenes in the presence of electrophilic or free radical agents.High optical purity can be incorporated into these products, starting with the readily available l-menthyl 6,6-dimethyl-2-oxobicyclohexane-1-carboxylate, the two diastereomers of which are chromatographically separable.Through suitable chemical correlation, the absolute configurations of the various enantiomers have beenmade known.Finally, a scheme for transforming the cyclopentenes to 1,1,2,3-tetrasubstituted cyclopentanes as a necessary prelude to a synthesis of retigeranic acid is detailed.
