Enantiopure derivatives of aza-Baylis-Hillman adducts by subsequent SN'-SN' reactions of acylcarbamates bearing a chiral auxiliary

Gianluca Martelli; Eleonora Marcucci; Mario Orena; Samuele Rinaldi

doi:10.3390/molecules14082824

Enantiopure derivatives of aza-Baylis-Hillman adducts by subsequent SN'-SN' reactions of acylcarbamates bearing a chiral auxiliary

Molecules. 2009 Jul 30;14(8):2824-35. doi: 10.3390/molecules14082824.

Authors

Gianluca Martelli¹, Eleonora Marcucci, Mario Orena, Samuele Rinaldi

Affiliation

¹ Dipartimento I.S.A.C. - Università Politecnica delle Marche, Via Brecce Bianche - I-60131 Ancona, Italy.

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aza Compounds / chemistry*
Carbamates / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Stereoisomerism

Substances

Aza Compounds
Carbamates