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

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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)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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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