J. M. Takacs, P. W. Newsome, C. Kuehn
1990
Citations
0
Influential Citations
26
Citations
Journal
Tetrahedron
Abstract
Abstract 2-Substituted-2,7,9-decatrienoates undergo an iron-catalyzed carbocyclization to yield trans -disubstituted cyclopentanes in moderate-to-good chemical yields. The cyclization products are formally the result of a [4+4]-ene reaction in which cis -propenyl and 2-acroyl functionalities are introduced as appendages to the newly formed cyclopentane ring by the cyclization. Triene ester substrates bearing an alkyl substituent at the 4- or 6-positions cyclize with high 1,2-stereoinduction to yield trisubstituted cyclopentanes in which the relative stereochemistry between three contiguous stereocenters is controlled.