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Convenient Asymmetric Synthesis of β-Trifluoromethyl-β-amino Acid, β-Amino Ketones, and γ-Amino Alcohols via Reformatsky and Mannich-Type Reactions from 2-Trifluoromethyl-1,3-oxazolidines

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    Convenient Asymmetric Synthesis of β-Trifluoromethyl-β-amino Acid, β-Amino Ketones, and γ-Amino Alcohols via Reformatsky and Mannich-Type Reactions from 2-Trifluoromethyl-1,3-oxazolidines
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    Laboratoire “Réactions Sélectives et Applications”, UMR CNRS 6519, Université de Reims-Champagne-Ardenne, Faculté des Sciences, BP 1039, 51687 Reims Cedex 2, France, and Laboratoire “Synthèse Organique Sélective et Chimie Organométallique” (SOSCO), UMR CNRS 8123, Université de Cergy-Pontoise, 5, Mail Gay-Lussac - Neuville sur Oise - 95031 Cergy-Pontoise Cedex, France [email protected]
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    Cite this: J. Org. Chem. 2006, 71, 5, 2159–2162
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    https://doi.org/10.1021/jo052323p
    Published February 2, 2006
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    The stereoselective syntheses of β-trifluoromethyl-β-amino ester, β lactams, and β-amino ketones starting from an oxazolidine derived from trifluoroacetaldehyde hemiacetal and (R)-phenylglycinol are reported. The Mannich-type reaction involving a chiral fluorinated iminium ion occurred in a good yield and with a higher stereoselectivity (dr up to 96:4) than that of the Reformatsky-type reaction. This straightforward strategy was applied to the short syntheses of (R)-3-amino-4,4,4-trifluorobutanoic acid, a series of novel enantiopure unprotected fluorinated β-amino ketones, and their corresponding γ-amino alcohols.

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     Université de Reims-Champagne-Ardenne.

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     To whom correspondence should be addressed. Phone:  + 33/(0)134257066. Fax:  + 33/(0)134257071.

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     Université de Cergy-Pontoise.

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2006, 71, 5, 2159–2162
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    https://doi.org/10.1021/jo052323p
    Published February 2, 2006
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