Asymmetric Synthesis of 3-Amine-tetrahydrothiophenes with a Quaternary Stereocenter via Nickel(II)/Trisoxazoline-Catalyzed Sulfa-Michael/Aldol Cascade Reaction: Divergent Access to Chiral Thionucleosides
Ke-Xin Huang, Ming‐Sheng Xie, Ji‐Wei Sang, Gui‐Rong Qu, Hai‐Ming Guo
Abstract
A generally useful Ni(II)/trisoxazoline-catalyzed asymmetric sulfa-Michael/Aldol cascade reaction is introduced to access chiral 3-amine-tetrahydrothiophene derivatives containing a quaternary stereocenter (32 examples, up to 93% yield, > 20:1 dr and 92% ee). Moreover, the novel strategy offers an efficient and convenient approach to construct chiral thionucleoside analogues.
Topics & Concepts
StereocenterTetrahydrothiopheneAldol reactionChemistryMichael reactionCascadeYield (engineering)Amine gas treatingCascade reactionCatalysisCombinatorial chemistryStereochemistryEnantioselective synthesisOrganic chemistryChromatographyMetallurgyMaterials scienceCyclopropane Reaction MechanismsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques