Synthesis of α-Hydroxy-β-triflamido Carboxylic Esters through Ring-Opening of Alkoxycarbonyl Oxiranes

Vittoria Lupi; Domenico Albanese; Dario Landini; Davide Scaletti; Michele Penso

doi:10.1055/s-2005-865285

PAPER

Synthesis of α-Hydroxy-β-triflamido Carboxylic Esters through Ring-Opening of Alkoxycarbonyl Oxiranes

Vittoria Lupi*^a, Domenico Albanese^a, Dario Landini^a, Davide Scaletti^a, Michele Penso*^b
^a Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, via Venezian 21, 20133 Milano, Italy
Fax: +39(02)50314159; e-Mail: vittoria.lupi@unimi.it;
^b CNR- Istituto di Scienze e Tecnologie Molecolari (ISTM), via Golgi 19, 20133 Milano, Italy
e-Mail: michele.penso@istm.cnr.it;

Abstract

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Abstract

The oxirane ring of 3-alkyl- and 3-arylglycidic esters has been opened with trifluoromethanesulfonamide (TfNH₂) under solid-liquid heterogeneous conditions. The corresponding α-hydroxy-β-triflamido esters were produced in good yields, in a regio- and stereoselective fashion. Several reaction parameters, such as the nature of the base, the presence of a phase transfer catalyst and/or a solvent have been examined.

Key words

regioselectivity - stereoselectivity - ring-opening - epoxides - amino acids

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References

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