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O-Alkylation versus C-alkylation under Mitsunobu conditions |
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| Authors: | Catalina Gurgui-Ionescu,Lycia Uttaro,Vé ronique Barragan-Montero |
| Affiliation: | a Equipe Glycochimie, Institut des Biomolécules Max Mousseron, UMR 5247 CNRS-UM1-UM2, ENSCM, CC 453, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex 5, France b GMCM UMR 6626, Campus de Beaulieu, 35042 Rennes Cedex, France c UMR CNRS 5253—ENSCM, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex 5, France |
| Abstract: | A comparative study of the Mitsunobu reaction at C1 and C6 positions of mannose using bis(2,2,2-trifluoroethyl) malonate as nucleophile is disclosed. While C-alkylation was predominant at the C6 position, only O-alkylation occurred at the anomeric position of the carbohydrate. Some factors playing a role in the selectivity of the reaction are discussed and an inverse mechanism of the Mitsunobu reaction for the anomeric position is proposed. |
| Keywords: | Mitsunobu reaction Ambident nucleophile C/O-Alkylation Steric and electronic effects |
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