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Chiral Brønsted acid from a cationic gold(I) complex: catalytic enantioselective protonation of silyl enol ethers of ketones.
J Am Chem Soc. 2011 Aug 31; 133(34):13248-51.JA

Abstract

A chiral Brønsted acid has been developed from a cationic gold(I) disphosphine complex in the presence of alcoholic solvent and applied to the enantioselective protonation reaction of silyl enol ethers of ketones. Various optically active cyclic ketones were obtained in excellent yields and high enantioselectivities, including cyclic ketones bearing aliphatic substrates at the α-position. Furthermore, the application of this Brønsted acid was extended to the first Brønsted acid-catalyzed enantioselective protonation reaction of silyl enol ethers of acyclic substrates, regardless of their E/Z ratio.

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Authors+Show Affiliations

Cheon CH
Department of Chemistry, University of California, Berkeley, California 94720, United States.
Kanno O
No affiliation info available
Toste FD
No affiliation info available

MeSH

AcidsCatalysisCationsEthersKetonesOrganogold CompoundsPhosphinesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

21815666

Citation

Cheon, Cheol Hong, et al. "Chiral Brønsted Acid From a Cationic gold(I) Complex: Catalytic Enantioselective Protonation of Silyl Enol Ethers of Ketones." Journal of the American Chemical Society, vol. 133, no. 34, 2011, pp. 13248-51.
Cheon CH, Kanno O, Toste FD. Chiral Brønsted acid from a cationic gold(I) complex: catalytic enantioselective protonation of silyl enol ethers of ketones. J Am Chem Soc. 2011;133(34):13248-51.
Cheon, C. H., Kanno, O., & Toste, F. D. (2011). Chiral Brønsted acid from a cationic gold(I) complex: catalytic enantioselective protonation of silyl enol ethers of ketones. Journal of the American Chemical Society, 133(34), 13248-51. https://doi.org/10.1021/ja204331w
Cheon CH, Kanno O, Toste FD. Chiral Brønsted Acid From a Cationic gold(I) Complex: Catalytic Enantioselective Protonation of Silyl Enol Ethers of Ketones. J Am Chem Soc. 2011 Aug 31;133(34):13248-51. PubMed PMID: 21815666.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Chiral Brønsted acid from a cationic gold(I) complex: catalytic enantioselective protonation of silyl enol ethers of ketones. AU - Cheon,Cheol Hong, AU - Kanno,Osamu, AU - Toste,F Dean, Y1 - 2011/08/04/ PY - 2011/8/6/entrez PY - 2011/8/6/pubmed PY - 2011/12/21/medline SP - 13248 EP - 51 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 133 IS - 34 N2 - A chiral Brønsted acid has been developed from a cationic gold(I) disphosphine complex in the presence of alcoholic solvent and applied to the enantioselective protonation reaction of silyl enol ethers of ketones. Various optically active cyclic ketones were obtained in excellent yields and high enantioselectivities, including cyclic ketones bearing aliphatic substrates at the α-position. Furthermore, the application of this Brønsted acid was extended to the first Brønsted acid-catalyzed enantioselective protonation reaction of silyl enol ethers of acyclic substrates, regardless of their E/Z ratio. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/21815666/Chiral_Brønsted_acid_from_a_cationic_gold_I__complex:_catalytic_enantioselective_protonation_of_silyl_enol_ethers_of_ketones_ L2 - https://doi.org/10.1021/ja204331w DB - PRIME DP - Unbound Medicine ER -