Nucleophilic Additions to N??Glycosylnitrones. Asymmetric Synthesis of α??Aminophosphonic Acids

…, A Knierzinger, JP Obrecht, A Vasella

Index: Huber, Rolf; Knierzinger, Andreas; Obrecht, Jean-Pierre; Vasella, Andrea Helvetica Chimica Acta, 1985 , vol. 68, p. 1730 - 1747

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Citation Number: 91

Abstract

Abstract The hypothesis which explains the diastereoselectivity of the 1, 3-dipolar cycloaddition of the N-glycosylnitrones 1–3 leading to the 5, 5-disubstituted isoxazolidines 4– 6 on the basis of a kinetic anomeric effect predicts that nucleophiles should add to N- glycosylnitrones with a high degree of diastereoselectivity. To test this prediction, the nucleophilic addition of lithium and potassium dialkylphosphites to the crystalline (Z)- ...

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