title: Silyllithium-Initiated Coupling of α-Ketoamides with tert-Butanesulfinylimines for Stereoselective Synthesis of Enantioenriched α-(Silyloxy)-β-amino Amides.
abstract: A silyllithium-initiated coupling of α-ketoamides with tert-butanesulfinylimines was developed for the efficient, stereoselective synthesis of enantioenriched α-(silyloxy)-β-amino amides. Nucleophilic addition of silyllithium to α-ketoamides, followed by 1,2-Brook rearrangement, generates nucleophilic enolates, which are then intercepted by chiral imines to provide three-component coupling products. Use of α-ketoamides is critical for achieving high yields and diastereoselectivities in the resulting α-hydroxy-β-amino acid derivatives.
authors.affiliation: Department of Chemistry and Applied Chemistry, Changji University , Changji 831100, China.
authors.forename: Zhao
authors.initials: Z
authors.lastname: Sun
authors.affiliation: The Key Laboratory of Plant Resources and Chemistry of Arid Zones, Xinjiang Technical Institute of Physics & Chemistry, Chinese Academy of Sciences , Urumqi 830011, China.
authors.forename: Hui
authors.initials: H
authors.lastname: Liu
authors.affiliation: Department of Chemistry and Applied Chemistry, Changji University , Changji 831100, China.
authors.forename: Yong-Ming
authors.initials: YM
authors.lastname: Zeng
authors.affiliation: Department of Chemistry and Applied Chemistry, Changji University , Changji 831100, China.|The Key Laboratory of Plant Resources and Chemistry of Arid Zones, Xinjiang Technical Institute of Physics & Chemistry, Chinese Academy of Sciences , Urumqi 830011, China.
authors.forename: Chong-Dao
authors.initials: CD
authors.lastname: Lu
authors.affiliation: The Key Laboratory of Plant Resources and Chemistry of Arid Zones, Xinjiang Technical Institute of Physics & Chemistry, Chinese Academy of Sciences , Urumqi 830011, China.
authors.forename: Yan-Jun
authors.initials: YJ
authors.lastname: Xu
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000577:Amides; D000596:Amino Acids; D007097:Imines; D017646:Organosilicon Compounds; D008094:Lithium