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Asymmetric Synthesis of Trisubstituted Tetrahydrothiophenes Bearing a Quaternary Stereocenter via Double Michael Reaction Involving Dynamic Kinetic Resolution

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posted on 05.07.2013, 00:00 by Sara Meninno, Gianluca Croce, Alessandra Lattanzi
The 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.