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Molecules 2009, 14(8), 2824-2835; doi:10.3390/molecules14082824

Enantiopure Derivatives of Aza-Baylis-Hillman Adducts by Subsequent SN′-SN′ Reactions of Acylcarbamates Bearing a Chiral Auxiliary

Dipartimento I.S.A.C. - Università Politecnica delle Marche, Via Brecce Bianche - I-60131 Ancona, Italy
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Received: 7 July 2009 / Revised: 22 July 2009 / Accepted: 30 July 2009 / Published: 30 July 2009
(This article belongs to the Special Issue Baylis-Hillman Reaction and Related Processes)
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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.
Keywords: chiral auxiliary; aza-Baylis-Hillman; rearrangement chiral auxiliary; aza-Baylis-Hillman; rearrangement
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Martelli, G.; Marcucci, E.; Orena, M.; Rinaldi, S. Enantiopure Derivatives of Aza-Baylis-Hillman Adducts by Subsequent SN′-SN′ Reactions of Acylcarbamates Bearing a Chiral Auxiliary. Molecules 2009, 14, 2824-2835.

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