Bicyclo[3.2.1]oct-6-enes via (3+2)cycloaddition

✍ Scribed by Brian D. Gray; Catherine M. McMillan; J.Allen Miller; Michael Moore

• Publisher: Elsevier Science
• Year: 1987
• Tongue: French
• Weight: 210 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)95695-8

✦ Synopsis

3+2)Cycloaddition of alkynes to ally1 cations, generated from 3-chlorocyclohexenes and zinc chloride, provides a simple and direct route to bicyclo[3.2.l]oct-6-enes. Bicyclo[3.2.l]octane derivatives are of interest because of their occurrence in natural product structures , many of which are of biological' or medicinal 2 consequence, and because this relatatively rigid ring system permits the study of stereochemical aspects of structure and reactivity. 3 Despite this interest, synthetic routes to this ring system are not numerous, and many are of limited application, and not appropriate to the synthesis of simple derivatives of the bicyclo[3.2.l]octane family. 4 Recent work by several groups has improved this situation somewhat, with reports of novel cyclisations 5