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

Yamamoto, Yasunori; Kurihara, Kazunori; Yamada, Akihiko; Takahashi, Miki; Takahashi, Youichi; Miyaura, Norio

doi:10.1016/S0040-4020(02)01557-0


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

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Title:	Intramolecular allylboration of γ-(ω-formylalkoxy)allylboronates for syntheses of trans- or cis-2-(ethenyl)tetrahydropyran-3-ol and 2-(ethenyl)oxepan-3-ol
Authors:	Yamamoto, Yasunori Browse this author →KAKEN DB
	Kurihara, Kazunori Browse this author
	Yamada, Akihiko Browse this author
	Takahashi, Miki Browse this author
	Takahashi, Youichi Browse this author
	Miyaura, Norio Browse this author
Keywords:	allylboration
	pinacolborane
	iridium-catalyzed isomerization
Issue Date:	20-Jan-2003
Publisher:	Elsevier Science Ltd.
Journal Title:	Tetrahedron
Volume:	59
Issue:	4
Start Page:	537
End Page:	542
Publisher DOI:	10.1016/S0040-4020(02)01557-0
Abstract:	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 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 90°C.
Relation:	http://www.sciencedirect.com/science/journal/00404020
Type:	article (author version)
URI:	http://hdl.handle.net/2115/15834
Appears in Collections:	工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 宮浦憲夫

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