title: Use of lithiated chiral o-sulfinylbenzyl carbanions for the one-pot building of linear fragments containing up to four connected stereocenters.
abstract: The reaction of o-sulfinylbenzyl carbanions with prochiral Michael acceptors, such as differently sized cycloalkenones, proceeded with high levels of stereoselectivity, generating molecules containing up to three asymmetric carbon centers in just one synthetic step. All these reactions involved the use of either a proton or an acylating reagent as the final electrophile. Furthermore, the trapping of the enolate resulting from Michael addition with prochiral electrophiles, such as aldehydes or N-sulfonylimines, allowed the highly stereoselective synthesis of densely functionalized compounds containing four chiral centers in just a one-pot sequence, the stereochemical outcome of the sequence being controlled by the sulfinyl auxiliary.
authors.affiliation: Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain. joseluis.garcia.ruano@uam.es
authors.forename: José Luis
authors.initials: JL
authors.lastname: García Ruano
authors.forename: Esther
authors.initials: E
authors.lastname: Torrente
authors.forename: Ana M
authors.initials: AM
authors.lastname: Martín-Castro
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D018020:Lithium Compounds / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D001593:Benzyl Compounds; D018020:Lithium Compounds; D013438:Sulfhydryl Compounds; D002244:Carbon