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The reaction between an acyl derivative of N-hydroxypyridine-2(1H)-thione (a Barton PTOC ester) and either an amine (primary or secondary), or the corresponding sulfenamide, led to the formation of a carboxamide in a clean transformation requiring minimal work-up and purification. The reaction with a sulfenamide is particularly useful since the only by-product, an unsymmetrical disulfide, is of both...
The N-hydroxypyridine-2(1H)-thione derivatives of two urethane-protected α-amino acids readily reacted with free α-amino acid esters or the corresponding benzenesulfenamides to give simple dipeptides in reasonable yields. The benzenesulfenamides are the reagents of choice since they allowed for neutral reaction conditions and exhibited superior reactivity in sterically demanding instances. The atom-economical...
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