Molecules 2009, 14(8), 2824-2835; doi:10.3390/molecules14082824
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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
* Author to whom correspondence should be addressed.
Received: 7 July 2009; in revised form: 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

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MDPI and ACS Style

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.

AMA Style

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(8):2824-2835.

Chicago/Turabian Style

Martelli, Gianluca; Marcucci, Eleonora; Orena, Mario; Rinaldi, Samuele. 2009. "Enantiopure Derivatives of Aza-Baylis-Hillman Adducts by Subsequent SN′-SN′ Reactions of Acylcarbamates Bearing a Chiral Auxiliary." Molecules 14, no. 8: 2824-2835.

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