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Chiral cyclopentadienylruthenium sulfoxide catalysts for asymmetric redox bicycloisomerization
- Source :
- Beilstein Journal of Organic Chemistry, Beilstein Journal of Organic Chemistry, Vol 12, Iss 1, Pp 1136-1152 (2016)
- Publication Year :
- 2016
- Publisher :
- Beilstein Institut, 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.
- Subjects :
- sulfoxide
Alkyne
010402 general chemistry
01 natural sciences
Full Research Paper
lcsh:QD241-441
ruthenium catalysis
chemistry.chemical_compound
Cycloisomerization
lcsh:Organic chemistry
cycloisomerization
Moiety
Organic chemistry
lcsh:Science
[4.1.0] bicycles
chemistry.chemical_classification
010405 organic chemistry
Organic Chemistry
Enantioselective synthesis
asymmetric catalysis
1,7-enyne
Sulfoxide
Combinatorial chemistry
Cycloaddition
0104 chemical sciences
3. Good health
Sulfonamide
Chemistry
1,6-enyne
chemistry
Propargyl
lcsh:Q
[3.1.0] bicycles
Subjects
Details
- ISSN :
- 18605397
- Volume :
- 12
- Database :
- OpenAIRE
- Journal :
- Beilstein Journal of Organic Chemistry
- Accession number :
- edsair.doi.dedup.....6c441bee6a551676909e238171d4a11f