Enantiopure derivatives of aza-Baylis-Hillman adducts by subsequent SN'-SN' reactions of acylcarbamates bearing a chiral auxiliary.
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.
Martelli
Gianluca
G
Dipartimento I.S.A.C. - Università Politecnica delle Marche, Via Brecce Bianche - I-60131 Ancona, Italy.
Marcucci
Eleonora
E
Orena
Mario
M
Rinaldi
Samuele
S
D001372:Aza Compounds / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D001372:Aza Compounds; D002219:Carbamates
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