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Versatile solid-phase synthesis of secondary amines from alcohols. Development of an N-Boc-(o-nitrobenzene)sulfonamide linker

✍ Scribed by Miles S. Congreve; Corinne Kay; Jan J. Scicinski; Steven V. Ley; Geoffrey Williams; Peter J. Murray; Stephen C. McKeown; Stephen P. Watson

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 256 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)00574-4

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✦ Synopsis

The development of a versatile amine releasing linker based on the modified o-nitrobenzene sulfonamide protective group is described. This new N-Boc-o-nitrobenzenesulfonamide (Boc-ONBS) linker enables the elaboration on resin of primary and secondary amines by sequential substitution of the sulfonamide moiety using the Mitsunobu reaction. A 16-member array of secondary and Boc protected primary amines was then prepared using this linker.