Carbohydrate-Based Spiro-1,3-oxazolidine-2-thiones:
Stereoselective Approaches Using Aziridines and Epoxides

Sébastien Tardy; Joana Lobo Vicente; Arnaud Tatibouët; Gilles Dujardin; Patrick Rollin

doi:10.1055/s-2008-1067266

PAPER

Carbohydrate-Based Spiro-1,3-oxazolidine-2-thiones: Stereoselective Approaches Using Aziridines and Epoxides

Sébastien Tardy^a, Joana Lobo Vicente^a, Arnaud Tatibouët*^a, Gilles Dujardin^b, Patrick Rollin^a
^a ICOA UMR 6005 CNRS, Université d’Orléans, 45067 Orléans, France
e-Mail: arnaud.tatibouet@univ-orleans.fr;
^b UCO2M UMR 6011 CNRS, Université du Maine, 72085 Le Mans, France

Abstract

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Abstract

d-glucose and d-fructose have been used as starting materials to prepare spiro-1,3-oxazolidine-2-thiones anchored on the third position of both carbohydrates. Following different approaches and depending on the carbohydrate template explored, stereoselective reactions have been developed via the formation of epoxides or aziridines.

Key words

azide - epoxide - spiro-compounds - chirality

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