title: 5-Endo-Trig Radical Cyclizations of Bromomethyldimethylsilyl Diisopropylpropargylic Ethers. A Highly Diastereoselective Access to Functionalized Cyclopentanes.
abstract: An efficient radical sequence involving a 5-exo-dig, a diastereoselective 1,5-H transfer, and a rarely observed in an all-carbon system 5-endo-trig cyclization allows the construction of cyclopentyl derivatives 2 bearing four controlled stereogenic centers from diisopropyl precursors 1. Olefins 3 were also isolated as minor side products. The effect of the acetylenic substituent Y has been investigated, and the scope and the limitations of the cascade have been delineated.
authors.affiliation: Laboratoire de Chimie Organique de Synthèse associé au CNRS, Université Pierre et Marie Curie, 4, place Jussieu - Tour 44-54, Case 229, 75252 Paris Cedex 05, France.
authors.forename: Stéphane
authors.initials: S
authors.lastname: Bogen
authors.forename: Mihaela
authors.initials: M
authors.lastname: Gulea
authors.forename: Louis
authors.initials: L
authors.lastname: Fensterbank
authors.forename: Max
authors.initials: M
authors.lastname: Malacria