title: An approach to the stereoselective synthesis of enantiopure dihydropyrroles and aziridines from a common sulfinyl-sulfinamide intermediate.
abstract: The diastereoselective addition of lithiated vinyl sulfoxides to enantiopure sulfinimines provides direct access to a wide assortment of allylic sulfinamides in good yields and excellent selectivities. These adducts are key precursors to differently functionalized cis- and trans-dihydropyrroles. Modulation of the protecting group on nitrogen prior to cyclization has a significant impact on the stereochemical outcome, allowing for the selective preparation of 2,5-cis- or 2,5-trans-3-sulfinyl disubstituted dihydropyrroles from a common sulfinamide intermediate. Further research on halocyclization conditions has also yielded a stereoselective synthesis of trisubstituted vinyl aziridines from these chiral sulfinamides, simply by changing the halogenating agent.
authors.affiliation: Instituto de Química Orgánica, IQOG-CSIC, Juan de la Cierva, 3, 28006 Madrid, Spain. iqov379@iqog.csic.es
authors.forename: Alma
authors.initials: A
authors.lastname: Viso
authors.forename: Roberto
authors.initials: R
authors.lastname: Fernández de la Pradilla
authors.forename: Mercedes
authors.initials: M
authors.lastname: Ureña
authors.forename: Robert H
authors.initials: RH
authors.lastname: Bates
authors.forename: Miguel A
authors.initials: MA
authors.lastname: del Águila
authors.forename: Ignacio
authors.initials: I
authors.lastname: Colomer