title: Exploiting the ring strain in bicyclo[2.2.1]heptane systems for the stereoselective preparation of highly functionalized cyclopentene, dihydrofuran, pyrroline, and pyrrolidine scaffolds.
abstract: The high strain of bicyclic systems drives retro-condensation reactions on bridgehead substituted bicyclo[2.2.1]hept-2-enes giving rise to orthogonally functionalized cyclopentene, 2,5-dihydrofuran, and 3-pyrroline scaffolds. Retro-Dieckman reactions were easily carried out on 3-tosyl-(7-carba/7-oxa/7-aza)bicyclo[2.2.1]hept-5-en-2-ones. Retro-aldol reactions of N-Boc-3-tosyl-7-azabicyclo[2.2.1]hept-5-en-2-ol and functionalized N-Boc-3-tosyl-7-azabicyclo[2.2.1]heptan-2-ols yield functionalized pyrrolidine scaffolds stereoselectively. The same reaction does not work with corresponding norbornene and 7-oxanorbornene derivatives.
authors: Department of Organic Chemistry, Faculty of Chemistry, University of Seville, Prof. García González, 1, 41012-Seville, Spain.
authors: Elena
authors: E
authors: Moreno-Clavijo
authors: Antonio J
authors: AJ
authors: Moreno-Vargas
authors: Raphaëlle
authors: R
authors: Kieffer
authors: Thérèse
authors: T
authors: Sigstam
authors: Ana T
authors: AT
authors: Carmona
authors: Inmaculada
authors: I
authors: Robina