ol4014975_si_002.cif (15.84 kB)
Asymmetric Synthesis of Trisubstituted Tetrahydrothiophenes Bearing a Quaternary Stereocenter via Double Michael Reaction Involving Dynamic Kinetic Resolution
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posted on 2013-07-05, 00:00 authored by Sara Meninno, Gianluca Croce, Alessandra LattanziThe stereoselective synthesis of highly functionalized tetrahydrothiophenes bearing three contiguous stereocenters, one of them quaternary, can be achieved by reacting trans-α-cyano-α,β-unsaturated ketones and trans-tert-butyl 4-mercapto-2-butenoate in the presence of a readily available amine thiourea. The products are obtained in high yield, good diastereoselectivity, and excellent enantioselectivity. The overall formation of tetrahydrothiophenes occurs via a cascade double Michael reaction involving a highly efficient process of dynamic kinetic resolution.
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enantioselectivitytranstereocentermercaptopresenceketoneTrisubstituted Tetrahydrothiophenes BearingDouble Michael ReactionAsymmetric Synthesisfunctionalized tetrahydrothiophenesdiastereoselectivityformationMichael reactionQuaternary Stereocenteramine thioureacascadeDynamic Kinetic ResolutionThe stereoselective synthesisquaternary
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