%0 Journal Article %A Moreno-Clavijo, Elena %A Moreno-Vargas, Antonio J. %A Kieffer, Raphaëlle %A Sigstam, Thérèse %A Carmona, Ana T. %A Robina, Inmaculada %D 2011 %T Exploiting the Ring Strain in Bicyclo[2.2.1]heptane Systems for the Stereoselective Preparation of Highly Functionalized Cyclopentene, Dihydrofuran, Pyrroline, and Pyrrolidine Scaffolds %U https://acs.figshare.com/articles/journal_contribution/Exploiting_the_Ring_Strain_in_Bicyclo_2_2_1_heptane_Systems_for_the_Stereoselective_Preparation_of_Highly_Functionalized_Cyclopentene_Dihydrofuran_Pyrroline_and_Pyrrolidine_Scaffolds/2576293 %R 10.1021/ol2027009.s001 %2 https://acs.figshare.com/ndownloader/files/4219834 %K Stereoselective Preparation %K orthogonally functionalized cyclopentene %K functionalized pyrrolidine scaffolds stereoselectively %K Pyrrolidine ScaffoldsThe %K Functionalized Cyclopentene %K Ring Strain %X 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. %I ACS Publications