title: Catalytic asymmetric construction of spiro(γ-butyrolactam-γ-butyrolactone) moieties through sequential reactions of cyclic imino esters with Morita-Baylis-Hillman bromides.
abstract: Spiro(γ-butyrolactam-γ-butyrolactone): a route to enantioenriched spiro(γ-butyrolactam-γ-butyrolactone) compounds, a valuable motif for drug discovery, was developed by use of a highly efficient copper(I)/TF-BiphamPhos-catalyzed tandem Michael addition-elimination of homoserine lactone derived cyclic imino esters with Morita-Baylis-Hillman (MBH) bromides, followed by treatment with para-toluenesulfonic acid.
authors.affiliation: College of Chemistry and Molecular Sciences, Wuhan University, PR China.
authors.forename: Huai-Long
authors.initials: HL
authors.lastname: Teng
authors.forename: He
authors.initials: H
authors.lastname: Huang
authors.forename: Chun-Jiang
authors.initials: CJ
authors.lastname: Wang
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry*; D001557:Benzenesulfonates / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry*; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry*; D004952:Esters; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001557:Benzenesulfonates; D001965:Bromides; D056831:Coordination Complexes; D004952:Esters; D007097:Imines; D013141:Spiro Compounds; C549499:TF-BiphamPhos; C088386:homoserine lactone; D015107:4-Butyrolactone; C029501:4-toluenesulfonic acid