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

doi:10.3390/feb97p5

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

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

Vladimir Ondrus* and Lubor Fisera*

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

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MDPI and ACS Style

Ondrus, V.; Fisera, L. Synthesis and 1,3-Dipolar Cycloaddition Reactions of Chiral Maleimides. Molecules 1997, 2, 49-56.

AMA Style

Ondrus V, Fisera L. Synthesis and 1,3-Dipolar Cycloaddition Reactions of Chiral Maleimides. Molecules. 1997; 2(2):49-56.

Chicago/Turabian Style

Ondrus, Vladimir; Fisera, Lubor. 1997. "Synthesis and 1,3-Dipolar Cycloaddition Reactions of Chiral Maleimides." Molecules 2, no. 2: 49-56.

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