Tetrahedron

A new method for synthesis of allenes, including an optically active form, from aldehydes and alkenyl aryl sulfoxides by sulfoxide–metal exchange as the key reaction …

T Satoh, N Hanaki, Y Kuramochi, Y Inoue, K Hosoya…

文献索引：Satoh, Tsuyoshi; Hanaki, Noriko; Kuramochi, Yuko; Inoue, Yujiro; Hosoya, Kayo; Sakai, Ken Tetrahedron, 2002 , vol. 58, # 13 p. 2533 - 2549

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被引用次数: 60

摘要

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 ...