Sulphenamides as synthetic precursors of aminyl radicals

doi:10.1016/0040-4039(91)80190-H

Tetrahedron Letters

Volume 32, Issue 44, 28 October 1991, Pages 6441-6444

https://doi.org/10.1016/0040-4039(91)80190-H Get rights and content

Abstract

Sulphenamides, readily synthesised from reaction between benzenesulphenyl derivatives and amines, undergo facile reaction with radical generating reagents such as tributyltin hydride to yield aminyl radicals.

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α-Chiral aminyl radicals have been generated from sulfenamides of α-amino acid esters and α-phenylethylamine using Bu₃SnH. The aminyl radicals of α-amino acid esters undergo 5-exo-trig cyclisation reactions onto side chain alkenes to yield proline analogues with reasonable diastereoselectivity. Preliminary studies show urethanyl radicals generated from sulfenamides of alkenyl urethane derivatives of α-amino acid esters and α-phenylethylamine undergo 5-exo-rig cyclisations to providing a protocol for the radical amination of unactivated alkenes. The α-ester of the amino acid or the urethane groups impart electrophilic behaviour to the aminyl radicals and facilitates cyclisation onto alkenes.
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Sulphenamides as synthetic precursors of aminyl radicals

Abstract

J. Am. Chem. Soc.

Tetrahedron

Aust. J. Chem.

J. Am. Chem. Soc.

Synthesis

Synthesis

Tetrahedron

Tetrahedron

Tetrahedron

Tetrahedron Lett.

Can. J. Chem.