Tetrahedron p. 5507 - 5522 (1990)
Update date:2022-08-02
Topics:
Takacs, James M.
Newsome, Peter W.
Kuehn, Cynthia
Takusagawa, Fusao
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.
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