Highly Substituted Homoallylvinylcyclopropanes by Indium-Mediated Reaction of α,β-Unsaturated Ketones and Aldehydes with Allylic Halides

✍ Scribed by Stephen M. Capps; Timothy P. Clarke; Jonathan P. H. Charmant; Henning A. F. Höppe; Guy C. Lloyd-Jones; Martin Murray; Torren M. Peakman; Rosie A. Stentiford; Kenneth E. Walsh; Paul A. Worthington

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 477 KB
• Volume: 2000
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(200003)2000:6<963::aid-ejoc963>3.0.co;2-1

✦ Synopsis

Allylindium reagents, prepared from excess allylic halide (Br or I) and indium metal, react with α,β-unsaturated ketones and aldehydes to give, after aerobic acidic workup, homoallyl-substituted vinylcyclopropanes. This process was explored and developed after a chance discovery arising from a side reaction in an attempted Pd-catalysed process. The structure of the cyclopropane arising from the reaction of bis(p-chlorobenzylidine)acetone was confirmed by X-ray