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A Brønsted acid catalyst for the enantioselective protonation reaction.
J Am Chem Soc. 2008 Jul 23; 130(29):9246-7.JA

Abstract

A highly reactive and robust chiral Brønsted acid catalyst, chiral N-triflyl thiophosphoramide, was developed. The first metal-free Brønsted acid catalyzed enantioselective protonation reaction of silyl enol ethers was demonstrated using this chiral Brønsted acid catalyst. The catalyst loading could be reduced to 0.05 mol % without any deleterious effect on the enantioselectivity.

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Authors+Show Affiliations

Cheon CH
Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
Yamamoto H
No affiliation info available

MeSH

AmidesCatalysisEthersPhosphoramidesPhosphoric AcidsProtonsSilanesStereoisomerismSulfhydryl Compounds

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

18582053

Citation

Cheon, Cheol Hong, and Hisashi Yamamoto. "A Brønsted Acid Catalyst for the Enantioselective Protonation Reaction." Journal of the American Chemical Society, vol. 130, no. 29, 2008, pp. 9246-7.
Cheon CH, Yamamoto H. A Brønsted acid catalyst for the enantioselective protonation reaction. J Am Chem Soc. 2008;130(29):9246-7.
Cheon, C. H., & Yamamoto, H. (2008). A Brønsted acid catalyst for the enantioselective protonation reaction. Journal of the American Chemical Society, 130(29), 9246-7. https://doi.org/10.1021/ja8041542
Cheon CH, Yamamoto H. A Brønsted Acid Catalyst for the Enantioselective Protonation Reaction. J Am Chem Soc. 2008 Jul 23;130(29):9246-7. PubMed PMID: 18582053.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A Brønsted acid catalyst for the enantioselective protonation reaction. AU - Cheon,Cheol Hong, AU - Yamamoto,Hisashi, Y1 - 2008/06/27/ PY - 2008/6/28/pubmed PY - 2008/9/3/medline PY - 2008/6/28/entrez SP - 9246 EP - 7 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 130 IS - 29 N2 - A highly reactive and robust chiral Brønsted acid catalyst, chiral N-triflyl thiophosphoramide, was developed. The first metal-free Brønsted acid catalyzed enantioselective protonation reaction of silyl enol ethers was demonstrated using this chiral Brønsted acid catalyst. The catalyst loading could be reduced to 0.05 mol % without any deleterious effect on the enantioselectivity. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/18582053/A_Brønsted_acid_catalyst_for_the_enantioselective_protonation_reaction_ L2 - https://doi.org/10.1021/ja8041542 DB - PRIME DP - Unbound Medicine ER -