Exploiting the ring strain in bicyclo[2.2.1]heptane systems for the stereoselective preparation of highly functionalized cyclopentene, dihydrofuran, pyrroline, and pyrrolidine scaffolds |
| |
Authors: | Moreno-Clavijo Elena Moreno-Vargas Antonio J Kieffer Raphaëlle Sigstam Thérèse Carmona Ana T Robina Inmaculada |
| |
Affiliation: | Department of Organic Chemistry, Faculty of Chemistry, University of Seville, Prof. García González, 1, 41012-Seville, Spain. |
| |
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. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|