Electrophile‐induced cyclizations of silyl‐substituted 4‐alken‐1‐ols
- verfasst von
- Gunadi Adiwidjaja, H. Flörke, Andreas Kirschning, Ernst Schauman
- Abstract
Silyl‐substituted 4‐alken‐1‐ols cyclize in the presence of a wide range of electrophilic reagents to give substituted tetra‐hydrofurans. The silyl group accelerates ring closure by its β‐effect and its position determines the efficiency of stereo‐control. Thus, a vinylic silyl group as in 1, 3‐9 gives mixtures of 2,5‐disubstituted tetrahydrofurans 2, 10‐21, favoring formation of the trans isomer. In contrast, an allylic silyl group as in 28‐30 exerts a high degree of stereocontrol, generally affording 2,3‐trans‐disubstituted tetrahydrofurans 31‐36.
- Externe Organisation(en)
-
Universität Hamburg
Technische Universität Clausthal
- Typ
- Artikel
- Journal
- Liebigs Annalen
- Band
- 1995
- Seiten
- 501-507
- Anzahl der Seiten
- 7
- ISSN
- 0947-3440
- Publikationsdatum
- 23.02.1995
- Publikationsstatus
- Veröffentlicht
- Peer-reviewed
- Ja
- ASJC Scopus Sachgebiete
- Allgemeine Chemie
- Elektronische Version(en)
-
https://doi.org/10.1002/jlac.199519950369 (Zugang:
Unbekannt)
