title: A dual-catalysis approach to the asymmetric Steglich rearrangement and catalytic enantioselective addition of O-acylated azlactones to isoquinolines.
abstract: A dual-catalysis approach, namely the combination of an achiral nucleophilic catalyst and a chiral anion-binding catalyst, was applied to the Steglich rearrangement to provide α,α-disubstituted amino acid derivatives in a highly enantioselective fashion. Replacement of the nucleophilic co-catalyst for isoquinoline resulted in a divergent reaction pathway and an unprecedented transformation of O-acylated azlactones. This strategy provided highly substituted α,β-diamino acid derivatives with excellent levels of stereocontrol.
authors.affiliation: Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA.
authors.forename: Chandra Kanta
authors.initials: CK
authors.lastname: De
authors.forename: Nisha
authors.initials: N
authors.lastname: Mittal
authors.forename: Daniel
authors.initials: D
authors.lastname: Seidel
mesh_terms: D000215:Acylation; D002384:Catalysis; D007546:Isoquinolines / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007546:Isoquinolines; D007783:Lactones; D010100:Oxygen