The sulfoxide-metal exchange reaction of β-acetoxy sulfoxides or β-mesyloxy sulfoxides, which were derived from alkenyl aryl sulfoxides and aldehydes in two steps, with a Grignard reagent or alkyllithium at low temperature gave allenes in good yields. Optically active allenes were synthesized starting from optically active 2-substituted ethenyl p-tolyl sulfoxides. A synthesis of (-)-methyl (E)-2,4,5-tetradecatrienoate, a male bean weevil sex attractant, was realized by this method.
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry