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

被引：27

作者：

Yamamoto, Y ^{[1
]}

Kurihara, K ^{[1
]}

Yamada, A ^{[1
]}

Takahashi, M ^{[1
]}

Takahashi, Y ^{[1
]}

Miyaura, N ^{[1
]}

机构：

[1] Hokkaido Univ, Div Mol Chem, Fac Engn, Grad Sch Engn, Sapporo, Hokkaido 0608628, Japan

来源：

TETRAHEDRON | 2003年 / 59卷 / 04期

关键词：

allylboration; pinacolborane; iridium-catalyzed isomerization;

D O I：

10.1016/S0040-4020(02)01557-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

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)(2)CHCH2(CH2)(n)CH2OCH=CHCH(2)Bpin, 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 allylboration leading to the formation of trans-2-(ethenyl)tetrahydropyran-3-ol or 2-(ethenyl)oxepan-3-ol from 8 and the corresponding cis-isomers from 10 in the presence of Yb(OTf)(3) (20 mol%) in aqueous acetonitrile at 90degreesC. (C) 2003 Elsevier Science Ltd. All rights reserved.

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页码：537 / 542

页数：6

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