title: Enantiopure derivatives of aza-Baylis-Hillman adducts by subsequent SN'-SN' reactions of acylcarbamates bearing a chiral auxiliary.
abstract: Reactions of(4S,5R)-1-(3,4-Dimethyl-2-oxo-5-phenylimidazolidine)carbonyl-isocyanate (4) with appropriate Baylis-Hillman adducts 5 gave the corresponding acyl carbamates 6,7 as equimolar diastereomeric mixtures. These mixtures were treated with DABCO, to afford with moderate diastereoselection easily separable [2-(3",4"-dimethyl-2"-oxo-5"-phenylimidazolidine-1-carboxamido)(aryl)methyl]acrylates 8 and 9.
authors.affiliation: Dipartimento I.S.A.C. - Università Politecnica delle Marche, Via Brecce Bianche - I-60131 Ancona, Italy.
authors.forename: Gianluca
authors.initials: G
authors.lastname: Martelli
authors.forename: Eleonora
authors.initials: E
authors.lastname: Marcucci
authors.forename: Mario
authors.initials: M
authors.lastname: Orena
authors.forename: Samuele
authors.initials: S
authors.lastname: Rinaldi
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001372:Aza Compounds; D002219:Carbamates
references.citation: Curr Protein Pept Sci. 2005 Apr;6(2):151-69
references.pmid: 15853652
references.citation: Biopolymers. 2007 Jul;86(4):288-97
references.pmid: 17443711
references.citation: J Org Chem. 2000 Mar 10;65(5):1305-18
references.pmid: 10814090
references.citation: Org Lett. 2004 Jul 22;6(15):2571-4
references.pmid: 15255693
references.citation: Chem Rev. 2009 Jan;109(1):1-48
references.pmid: 19140772
references.citation: Curr Med Chem. 2000 Sep;7(9):945-70
references.pmid: 10911024