Tags

Type your tag names separated by a space and hit enter

Cinchona alkaloid-catalyzed asymmetric trifluoromethylation of alkynyl ketones with trimethylsilyl trifluoromethane.
Org Lett. 2010 Nov 19; 12(22):5104-7.OL

Abstract

The first catalytic enantioselective trifluoromethylation of alkynyl ketones 1 with (trifluoromethyl)trimethylsilane is disclosed by an operationally simple procedure, based on the combination of ammonium bromide of bis-cinchona alkaloids with Me(4)NF to afford trifluoromethyl-substituted tertiary propargyl alcohols (up to 96% ee), which are the important chiral building blocks for pharmaceuticals. Biologically attractive aryl heteroaryl trifluoromethyl carbinols were also synthesized.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Kawai H
Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.
Tachi K
No affiliation info available
Tokunaga E
No affiliation info available
Shiro M
No affiliation info available
Shibata N
No affiliation info available

MeSH

AlkynesBromidesCatalysisCinchona AlkaloidsCombinatorial Chemistry TechniquesKetonesMethanolMolecular StructurePropanolsQuaternary Ammonium CompoundsStereoisomerismTrimethylsilyl Compounds

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

20954725

Citation

Kawai, Hiroyuki, et al. "Cinchona Alkaloid-catalyzed Asymmetric Trifluoromethylation of Alkynyl Ketones With Trimethylsilyl Trifluoromethane." Organic Letters, vol. 12, no. 22, 2010, pp. 5104-7.
Kawai H, Tachi K, Tokunaga E, et al. Cinchona alkaloid-catalyzed asymmetric trifluoromethylation of alkynyl ketones with trimethylsilyl trifluoromethane. Org Lett. 2010;12(22):5104-7.
Kawai, H., Tachi, K., Tokunaga, E., Shiro, M., & Shibata, N. (2010). Cinchona alkaloid-catalyzed asymmetric trifluoromethylation of alkynyl ketones with trimethylsilyl trifluoromethane. Organic Letters, 12(22), 5104-7. https://doi.org/10.1021/ol102189c
Kawai H, et al. Cinchona Alkaloid-catalyzed Asymmetric Trifluoromethylation of Alkynyl Ketones With Trimethylsilyl Trifluoromethane. Org Lett. 2010 Nov 19;12(22):5104-7. PubMed PMID: 20954725.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Cinchona alkaloid-catalyzed asymmetric trifluoromethylation of alkynyl ketones with trimethylsilyl trifluoromethane. AU - Kawai,Hiroyuki, AU - Tachi,Kentaro, AU - Tokunaga,Etsuko, AU - Shiro,Motoo, AU - Shibata,Norio, Y1 - 2010/10/18/ PY - 2010/10/20/entrez PY - 2010/10/20/pubmed PY - 2011/1/15/medline SP - 5104 EP - 7 JF - Organic letters JO - Org Lett VL - 12 IS - 22 N2 - The first catalytic enantioselective trifluoromethylation of alkynyl ketones 1 with (trifluoromethyl)trimethylsilane is disclosed by an operationally simple procedure, based on the combination of ammonium bromide of bis-cinchona alkaloids with Me(4)NF to afford trifluoromethyl-substituted tertiary propargyl alcohols (up to 96% ee), which are the important chiral building blocks for pharmaceuticals. Biologically attractive aryl heteroaryl trifluoromethyl carbinols were also synthesized. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/20954725/Cinchona_alkaloid_catalyzed_asymmetric_trifluoromethylation_of_alkynyl_ketones_with_trimethylsilyl_trifluoromethane_ L2 - https://doi.org/10.1021/ol102189c DB - PRIME DP - Unbound Medicine ER -