This work is dedicated to the memory of David A. Evans for his commitment and lasting
contributions to research and teaching.
Abstract
Herein is reported a robust and general method for the preparation of N-acylsulfenamides, important functionalities that have recently been utilized as central
inputs for the asymmetric synthesis of high oxidation state sulfur compounds. This
straightforward transformation proceeds by reaction of primary amides, carbamates,
sulfonamides, sulfinamides, and ureas with stable N-thiosuccinimides or N-thiophthalimides, which in turn are prepared in a single step from commercial thiols.
The use of stable N-thiosuccinimide and N-thiophthalimide reactants is desirable because it obviates the use of highly reactive
sulfenyl chlorides.
Key words
sulfenamide - amide - thiosuccinimide - thiophthalimide - thiol - asymmetric catalysis
