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Convenient synthesis of alpha-trifluoromethylated acyloins from alpha-hydroxy or alpha-amino acids. 2000

M Kawase, and S Saito, and T Kurihara
Faculty of Pharmaceutical Sciences, Josai University, Sakado, Saitama, Japan. kawasema@josai.ac.jp

Alpha-trifluoromethylated acyloins (2 and 6) have been prepared from alpha-hydroxy acids (1), N-acylprolines (5) or N-acyl-N-alkyl alpha-amino acids (8) by novel transformation reactions with trifluoroacetic anhydride (TFAA) in the presence of pyridine. The former reaction of 1 could proceed through mesoionic 1,3-dioxolium-4-olates, whereas the latter two reactions of alpha-amino acids (5 and 8) could involve mesoionic 1,3-oxazolium-5-olates. The reaction of 1 with TFAA shows more potential for practical applications because of the ready availability of the starting materials and ease of manipulation.

UI MeSH Term Description Entries
D007202 Indicators and Reagents Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499) Indicator,Reagent,Reagents,Indicators,Reagents and Indicators
D008333 Mandelic Acids Analogs or derivatives of mandelic acid (alpha-hydroxybenzeneacetic acid). Acids, Mandelic
D005233 Fatty Alcohols Usually high-molecular-weight, straight-chain primary alcohols, but can also range from as few as 4 carbons, derived from natural fats and oils, including lauryl, stearyl, oleyl, and linoleyl alcohols. They are used in pharmaceuticals, cosmetics, detergents, plastics, and lube oils and in textile manufacture. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Fatty Alcohol,Alcohol, Fatty,Alcohols, Fatty
D005463 Fluoroacetates Derivatives of acetic acid with one or more fluorines attached. They are almost odorless, difficult to detect chemically, and very stable. The acid itself, as well as the derivatives that are broken down in the body to the acid, are highly toxic substances, behaving as convulsant poisons with a delayed action. (From Miall's Dictionary of Chemistry, 5th ed)
D005559 Formamides A group of amides with the general formula of R-CONH2.
D006845 Hydrocarbons, Fluorinated Inert liquid or gaseous halocarbon compounds in which FLUORINE replaces some or all HYDROGEN atoms. Fluorinated Hydrocarbons
D006880 Hydroxy Acids Organic compounds containing both the hydroxyl and carboxyl radicals. Hydroxy Acid,Acid, Hydroxy,Acids, Hydroxy
D000089 Acetic Anhydrides Compounds used extensively as acetylation, oxidation and dehydrating agents and in the modification of proteins and enzymes. Anhydrides, Acetic
D000596 Amino Acids Organic compounds that generally contain an amino (-NH2) and a carboxyl (-COOH) group. Twenty alpha-amino acids are the subunits which are polymerized to form proteins. Amino Acid,Acid, Amino,Acids, Amino

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