Synthesis of Vinylcyclopropanes from Epoxides

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

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  • Technische Universität Clausthal
  • Universität Hamburg
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Details

OriginalspracheEnglisch
Seiten (von - bis)717-723
Seitenumfang7
FachzeitschriftJournal of Organic Chemistry
Jahrgang56
Ausgabenummer2
PublikationsstatusVeröffentlicht - 1 Jan. 1991
Extern publiziertJa

Abstract

Ring-opening of epoxides 1 by heteroatom-substituted allylanions 2 occurs with high regioselectivity. In situ tosylation of the resulting alkoxides 3 or tosylation of the corresponding alcohols 4 yields 4-pentenyl tosylates 5. Anion generation by deprotonation or desilylation gives vinylcyclopropanes 9 by an SNi process. The approach allows annulation of vinylcyclopropanes onto existing five- and six-membered rings and synthesis of vinyl-cyclopropanes with functionality on the olefin.

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Synthesis of Vinylcyclopropanes from Epoxides. / Schaumann, Ernst; Kirschning, Andreas; Narjes, Frank.
in: Journal of Organic Chemistry, Jahrgang 56, Nr. 2, 01.01.1991, S. 717-723.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Schaumann E, Kirschning A, Narjes F. Synthesis of Vinylcyclopropanes from Epoxides. Journal of Organic Chemistry. 1991 Jan 1;56(2):717-723. doi: 10.1021/jo00002a043
Schaumann, Ernst ; Kirschning, Andreas ; Narjes, Frank. / Synthesis of Vinylcyclopropanes from Epoxides. in: Journal of Organic Chemistry. 1991 ; Jahrgang 56, Nr. 2. S. 717-723.
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