Electrophile‐induced cyclizations of silyl‐substituted 4‐alken‐1‐ols
- authored by
- 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.
- External Organisation(s)
-
Universität Hamburg
Clausthal University of Technology
- Type
- Article
- Journal
- Liebigs Annalen
- Volume
- 1995
- Pages
- 501-507
- No. of pages
- 7
- ISSN
- 0947-3440
- Publication date
- 23.02.1995
- Publication status
- Published
- Peer reviewed
- Yes
- ASJC Scopus subject areas
- General Chemistry
- Electronic version(s)
-
https://doi.org/10.1002/jlac.199519950369 (Access:
Unknown)
