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.
Monaco, Mattia Riccardo,Prvost, Sbastien,List, Benjamin
supporting information
p. 16982 - 16985
(2015/02/18)
A practical synthesis of differentially-protected cis-1,2-cyclopentanedithiols and cis-3,4-pyrrolidinedithiols
A practical method for the synthesis of cis-1,2-cyclopentanedithiols and cis-3,4-pyrrolidinedithiols with differentially protected sulfurs, needed for the design of new metal-chelating ligands, has been developed.
Jin, Yonghao,Ghaffari, Mohammad A,Schwartz, Martin A
p. 7319 - 7321
(2007/10/03)
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