Catalytic asymmetric addition of thiols to silyl glyoxylates for synthesis of multi-hetero-atom substituted carbon stereocenters
Mingming Guan, Shiyu Wang, Yao Luo, Weidi Cao, Xiaohua Liu, Xiaoming Feng
Abstract
A chiral Lewis acid-catalyzed enantioselective addition of thiols to silyl glyoxylates was developed. The reaction proceeds well with a broad range of thiols and acylsilanes, affording the target tertiary chiral α-silyl-α-sulfydryl alcohols with multi-hetero-atom carbon stereocenters in excellent yields (up to 99%) and enantioselectivities (up to 98% ee). A series of control experiments were conducted to elucidate the reaction mechanism.
Topics & Concepts
StereocenterEnantioselective synthesisSilylationCarbon atomCatalysisChemistryAtom (system on chip)Carbon fibersStereochemistryCombinatorial chemistryOrganic chemistryMaterials scienceComputer scienceRing (chemistry)Composite numberComposite materialEmbedded systemSulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsAsymmetric Synthesis and Catalysis