Alkoxyamine-cyanoborane adducts: efficient cyanoborane transfer agents.

Authors :: Márquez JM
Martínez-Castro E
Gabrielli S
López Ó
Maya I
Angulo M
Álvarez E
Fernández-Bolaños JG
Source :: Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2011 May 21; Vol. 47 (19), pp. 5617-9. Date of Electronic Publication: 2011 Apr 11.
Publication Year :: 2011
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.<br /> (© The Royal Society of Chemistry 2011)