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Chiral cyclopentadienylruthenium sulfoxide catalysts for asymmetric redox bicycloisomerization.
- Source :
-
Beilstein journal of organic chemistry [Beilstein J Org Chem] 2016 Jun 07; Vol. 12, pp. 1136-52. Date of Electronic Publication: 2016 Jun 07 (Print Publication: 2016). - Publication Year :
- 2016
-
Abstract
- A full account of our efforts toward an asymmetric redox bicycloisomerization reaction is presented in this article. Cyclopentadienylruthenium (CpRu) complexes containing tethered chiral sulfoxides were synthesized via an oxidative [3 + 2] cycloaddition reaction between an alkyne and an allylruthenium complex. Sulfoxide complex 1 containing a p-anisole moiety on its sulfoxide proved to be the most efficient and selective catalyst for the asymmetric redox bicycloisomerization of 1,6- and 1,7-enynes. This complex was used to synthesize a broad array of [3.1.0] and [4.1.0] bicycles. Sulfonamide- and phosphoramidate-containing products could be deprotected under reducing conditions. Catalysis performed with enantiomerically enriched propargyl alcohols revealed a matched/mismatched effect that was strongly dependent on the nature of the solvent.
Details
- Language :
- English
- ISSN :
- 1860-5397
- Volume :
- 12
- Database :
- MEDLINE
- Journal :
- Beilstein journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 27559366
- Full Text :
- https://doi.org/10.3762/bjoc.12.110