Conversion of Glycosyl Azides via N-Bromoglycosylimines to Aldononitriles

Fürstner, Alois; Praly, Jean-Pierre

doi:10.1002/anie.199407511

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Conversion of Glycosyl Azides via N-Bromoglycosylimines to Aldononitriles

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Fürstner, Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Fürstner, A., & Praly, J.-P. (1994). Conversion of Glycosyl Azides via N-Bromoglycosylimines to Aldononitriles. Angewandte Chemie International Edition in English, 33(7), 751-753. doi:10.1002/anie.199407511.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-A49E-5

Abstract

In a one-pot reaction, aldononitriles can be synthesized smoothly from glycosyl azides by successive treatment with N-bromosuccinimide (NBS) and activated metals M* [Eq. (a)]. By the correct choice of the reducing agent, the intermediate alcoholate can be trapped with electrophiles.