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Molecules 1997, 2(2), 49-56; doi:10.3390/feb97p5
Article

Synthesis and 1,3-Dipolar Cycloaddition Reactions of Chiral Maleimides

* and *
Department of Organic Chemistry, Slovak Technical University, SK-812 37 Bratislava, Slovak Republic
* Authors to whom correspondence should be addressed.
Received: 19 October 1996 / Accepted: 10 December 1996 / Published: 25 February 1997
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Abstract

New routes to the synthesis of various novel chiral maleimides are described. The oxabicyclic anhydride 2 readily available exo-Diels-Alder adduct of furan and maleic anhydride was used as a vehicle, which in turn reacted with hydrochlorides of amino acids 3a-f in the presence of Et3N with release of furan to give the requisite novel chiral imides 4a-f in good to moderate yields. The stereoselectivity of 1,3-dipolar cycloaddition of nitrile oxides with prepared chiral imides 4a-f is investigated.
Keywords: Chiral maleimides; 1; 3-dipolar cycloadditions; nitrile oxides; stereoselectivity Chiral maleimides; 1; 3-dipolar cycloadditions; nitrile oxides; stereoselectivity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Ondrus, V.; Fisera, L. Synthesis and 1,3-Dipolar Cycloaddition Reactions of Chiral Maleimides. Molecules 1997, 2, 49-56.

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