Issue 19, 2011
From the journal:

Chemical Communications

Alkoxyamine-cyanoborane adducts: efficient cyanoborane transfer agents†

José M. Márquez,a   Elisa Martínez-Castro,a   Serena Gabrielli,a   Óscar López,a   Inés Maya,a   Manuel Angulo,b   Eleuterio Álvarezc  and  José G. Fernández-Bolaños*a  

* Corresponding authors

a Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, c/Profesor García González 1, Seville, Spain
E-mail: bolanos@us.es
Fax: +34 954624960
Tel: +34 954550996

b Servicio de RMN, Universidad de Sevilla, Apartado 1152, Seville, Spain

c Instituto de Investigaciones Químicas “Isla de la Cartuja”, CSIC-USE, Américo Vespucio 49, Seville, Spain

Abstract

We report the synthesis of the hitherto unknown zwitterionic alkoxyamino cyanoboranes by reduction of O-alkyloximes with sodium cyanoborohydride; unprecedented cyanoboronated N-alkoxyformamidines were also isolated as by-products. Boronated alkoxyamines were found to be efficient cyanoborane transfer agents towards more basic amines, including aminosugars; they were also successfully transformed into neoglycoconjugates by the neoglycorandomization reaction with reducing sugars.

Graphical abstract: Alkoxyamine-cyanoborane adducts: efficient cyanoborane transfer agents

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Article information

DOI
https://doi.org/10.1039/C1CC11345C
Article type
Communication
Submitted
08 Mar 2011
Accepted
25 Mar 2011
First published
11 Apr 2011

Chem. Commun., 2011,47, 5617-5619

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Alkoxyamine-cyanoborane adducts: efficient cyanoborane transfer agents

J. M. Márquez, E. Martínez-Castro, S. Gabrielli, Ó. López, I. Maya, M. Angulo, E. Álvarez and J. G. Fernández-Bolaños, Chem. Commun., 2011, 47, 5617 DOI: 10.1039/C1CC11345C

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