Catalytic, enantioselective aldol additions to ketones

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Abstract

Catalytic, enantioselective additions of a trichlorosilyl ketene acetal to ketones have been demonstrated. The trichlorosilyl enolate of methyl acetate undergoes a rapid and high-yielding aldol addition to a wide range of ketones (aromatic, olefinic, acetylenic, aliphatic) in the presence of a catalytic amount of pyridine N-oxide. Moreover, in the presence of a catalytic amount (10 mol %) of a chiral bispyridine bis N-oxide (possessing both axial and central chiral elements) the aldol addition takes place again in excellent yield and with good stereoselectivity. The enantioselectivities of the additions are highly variable (7-86% ee) and are strongly dependent on the structure of the ketone acceptor. Aromatic methyl ketones gave the highest selectivity, whereas olefinic ketones were the least selective.

Original languageEnglish (US)
Pages (from-to)4233-4235
Number of pages3
JournalJournal of the American Chemical Society
Volume124
Issue number16
DOIs
StatePublished - Apr 24 2002

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ASJC Scopus subject areas

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

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