%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