A new method for synthesis of allenes, including an optically active form, from aldehydes and alkenyl aryl sulfoxides with carboncarbon bond-formation

✍ Scribed by Tsuyoshi Satoh; Yuko Kuramochi; Yujiro Inoue

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 206 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)01666-4

✦ Synopsis

Ligand exchange reaction of I~-mesyloxy sulfoxides or 13-acetoxy sulfoxides, which were derived from alkenyl aryl sulfoxides and aldehydes in two steps, with n-BuLi or EtMgBr at low temperature gave allenes in good yields. Optically active allenes were synthesized starting from optically active 2-phenylethenylp-tolyl sulfoxides.