Regio- and stereoselective cyclopropanation of functionalised dienes. Novel methodology for the synthesis of vinyl- and divinyl-cyclopropanes

✍ Scribed by István E. Markó; Thierry Giard; Shinichi Sumida; Anne-Elisabeth Gies

• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 132 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)00242-3

✦ Synopsis

Dienes, bearing an electron-withdrawing substituent at C-1, are cyclopropanated regio-and stereoselectively at the C C double bond proximal to this electron-withdrawing group. The highest selectivity is observed in the case of dienylboronates. The cyclopropanation of these substrates affords almost exclusively the synthetically useful 1-boronato-2-vinyl-cyclopropanes.