3551-50-6Relevant articles and documents
Catalytic asymmetric synthesis of thiols
Monaco, Mattia Riccardo,Prvost, Sbastien,List, Benjamin
supporting information, p. 16982 - 16985 (2015/02/18)
The synthesis of enantiopure thiols is of significant interest for industrial and academic applications. However, direct asymmetric approaches to free thiols have previously been unknown. Here we describe a novel organocascade that is catalyzed by a confined chiral phosphoric acid and furnishes O-protected β-hydroxythiols with excellent enantioselectivities. The method relies on an asymmetric thiocarboxylysis of meso-epoxides, followed by an intramolecular trans-esterification reaction. By varying the reaction conditions, the intermediate thioesters can also be obtained chemoselectively and enantioselectively.