Asymmetric synthesis of trisubstituted tetrahydrothiophenes bearing a quaternary stereocenter via double michael reaction involving dynamic kinetic resolution

Sara Meninno, Gianluca Croce, Alessandra Lattanzi

Risultato della ricerca: Contributo su rivistaArticolo in rivistapeer review

Abstract

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.

Lingua originaleInglese
pagine (da-a)3436-3439
Numero di pagine4
RivistaOrganic Letters
Volume15
Numero di pubblicazione13
DOI
Stato di pubblicazionePubblicato - 5 lug 2013
Pubblicato esternamente

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