Vol.32, No.3(4) [2010]

Synthesis and Stereochemical Behavior of Ketoester Derivatives having trans-Cyclononene Skeleton

Hiroko INOUE, Kazunobu IGAWA and Katsuhiko TOMOOKA


It has been found that the enolate formation followed by the alkylation of cyclic ketoester 2 provides (pR*, S*)-1 predominantly as a kinetic product. Planar chirality of 1 is labile at ambient temperature, hence (pR*, S*)-1 easily isomerizes to thermodynamically more favorable (pS*, S*)-1.