Chiral brønsted acid from a cationic gold(I) complex

Catalytic enantioselective protonation of silyl enol ethers of ketones

Cheol-Hong Cheon, Osamu Kanno, F. Dean Toste

Research output: Contribution to journalArticle

76 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)13248-13251
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number34
DOIs
Publication statusPublished - 2011 Aug 31
Externally publishedYes

Fingerprint

Ethers
Protonation
Ketones
Gold
Acids
Bearings (structural)
Enantioselectivity
Substrates

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Chiral brønsted acid from a cationic gold(I) complex : Catalytic enantioselective protonation of silyl enol ethers of ketones. / Cheon, Cheol-Hong; Kanno, Osamu; Toste, F. Dean.

In: Journal of the American Chemical Society, Vol. 133, No. 34, 31.08.2011, p. 13248-13251.

Research output: Contribution to journalArticle

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