Synthesis of Vinylcyclopropanes from Epoxides
- authored by
- Ernst Schaumann, Andreas Kirschning, Frank Narjes
- 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.
- External Organisation(s)
-
Clausthal University of Technology
Universität Hamburg
- Type
- Article
- Journal
- Journal of Organic Chemistry
- Volume
- 56
- Pages
- 717-723
- No. of pages
- 7
- ISSN
- 0022-3263
- Publication date
- 01.01.1991
- Publication status
- Published
- Peer reviewed
- Yes
- ASJC Scopus subject areas
- Organic Chemistry
- Electronic version(s)
-
https://doi.org/10.1021/jo00002a043 (Access:
Unknown)
