Reactivity of substituted 3-(diethylphosphonyl)-1-(trialkylsilyl)alka-1,3-dienes: Regioselective epoxidation and cyclopropanation reactions

✍ Scribed by Fabien Chevalier; Hashim Al-Badri; Noël Collignon

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 176 KB
• Volume: 10
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/(sici)1098-1071(1999)10:3<231::aid-hc9>3.0.co;2-6

✦ Synopsis

When treated with electrophilic m-CPBA reagent, dienes 1 were efficiently epoxidized at the silylated 1,2-double bond exclusively. Otherwise, regioselective cyclopropanation of the phosphonylated 3,4-double bond was achieved by using the nucleophilic Corey's reagent.