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Asymmetric Friedel-Crafts Alkylation of Indoles with Trifluoromethyl Pyruvate Catalyzed by a Dinuclear Zinc Catalyst.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2018 Feb 02; Vol. 83 (3), pp. 1160-1166. Date of Electronic Publication: 2018 Jan 16. - Publication Year :
- 2018
-
Abstract
- A bimetallic cooperative catalysis model has been reported for the asymmetric Friedel-Crafts (F-C) alkylation of indoles with trifluoromethyl pyruvates using Trost's intramolecular dinuclear zinc complex as the catalyst. This dinuclear zinc catalyst was prepared in situ by reacting the chiral ligand (S,S)-L2b with 2 equiv of ZnEt <subscript>2</subscript> . A series of trifluoromethyl alcohol and indole-containing biological compounds were formed in moderate to good yields (up to 95%) with good enantioselectivity (up to 88% enantiomeric excess (ee)) in the presence of 10 mol % catalyst under mild conditions. A synergistic transition state model was proposed to explain the origin of the asymmetric induction.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 83
- Issue :
- 3
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 29294293
- Full Text :
- https://doi.org/10.1021/acs.joc.7b02599