Iridium-catalyzed asymmetric allylation of sodium triisopropylsilanethiolate: A new way to form chiral thiols

Abstract

The iridium phosphoramidite complex-promoted regio- and enantioselective reaction of allylic carbonates with sodium triisopropylsilanethiolate produced allylic sulfides in 40–77% yields with up to 97 : 3 (branched : linear) and 89% ee, which were readily transformed into chiral thiol in 68% yield with 87% ee or disulfides with two chiral C–S bond centers in 40–73% yields with up to 90 : 10 dr and 99% ee.