Radical amination with sulfonyl azides: a powerful method for the formation of C-N bonds.
A novel reaction for the introduction of an azide moiety by means of a mild radical process is currently under development. Sulfonyl azides are suitable azidating agents for nucleophilic radicals, such as secondary and tertiary alkyl radicals. More electrophilic radicals, such as enolate radicals, do not react with sulfonyl azides. This feature allowed the development of efficient intra- and intermolecular carboazidations of olefins. Due to the versatility of the azido group, this reaction has an important synthetic potential, as already demonstrated by the preparation of the core of several alkaloids, particularly those containing an amino-substituted quaternary carbon center, such as FR901483.
University of Bern, Department of Chemistry and Biochemistry, Freiestrasse 3, 3000 Bern 9, Switzerland. philippe.renaud@ioc.unibe.ch
Philippe
P
Panchaud
Laurent
L
Chabaud
Yannick
Y
Landais
Cyril
C
Ollivier
Philippe
P
Renaud
Sarunas
S
Zigmantas