Tetrahedron

Intramolecular allylboration of γ-(ω-formylalkoxy) allylboronates for syntheses of trans-or cis-2-(ethenyl) tetrahydropyran-3-ol and 2-(ethenyl) oxepan-3-ol

Y Yamamoto, K Kurihara, A Yamada, M Takahashi…

文献索引：Yamamoto, Yasunori; Kurihara, Kazunori; Yamada, Akihiko; Takahashi, Miki; Takahashi, Youichi; Miyaura, Norio Tetrahedron, 2003 , vol. 59, # 4 p. 537 - 542

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被引用次数: 31

摘要

3-Alkoxy-1-alkynes 4 were hydroborated with pinacolborane (HBpin) to give 3-alkoxy-1- alkenylboronates 5. The latter gave (E)-3-alkoxyallylboronates (8:(E)-(MeO) 2CHCH2 (CH2) nCH2OCH CHCH2Bpin, n= 1–3) when they were subjected to iridium-catalyzed isomerization of the double bond. The corresponding (Z)-isomers 10 were synthesized by nickel-catalyzed isomerization of 5. Both allylboronates underwent intramolecular ...