An Unusual and Stereoselective Michael Addition of αAmino Ester-Derived N-Lithiated Azomethine Ylides

Adrien      Soret; Luis      Blanco; Sandrine      Deloisy

doi:10.2174/157017806778700006

Abstract

N-Lithiated azomethine ylides generated from N-arylidene-α-amino esters react on their Cγ:-atom with a 7-oxabicyclo[2.2.1]heptadiene derived diester. This regio- and stereoselective Michael addition yields β-amino diesters after acidic work-up. Retro-Diels-Alder reaction from these amines or related amides allows the preparation of (aminomethyl)maleate derivatives.

Keywords: Azomethine ylides, N-arylidene-a-amino esters, 1,3-dipolar cycloaddition, Michael addition, retro-Diels-Alder reaction

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Letters in Organic Chemistry

Title: An Unusual and Stereoselective Michael Addition of αAmino Ester-Derived N-Lithiated Azomethine Ylides

Volume: 3 Issue: 9

Author(s): Adrien Soret, Luis Blanco and Sandrine Deloisy

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Keywords: Azomethine ylides, N-arylidene-a-amino esters, 1,3-dipolar cycloaddition, Michael addition, retro-Diels-Alder reaction

Abstract: N-Lithiated azomethine ylides generated from N-arylidene-α-amino esters react on their Cγ:-atom with a 7-oxabicyclo[2.2.1]heptadiene derived diester. This regio- and stereoselective Michael addition yields β-amino diesters after acidic work-up. Retro-Diels-Alder reaction from these amines or related amides allows the preparation of (aminomethyl)maleate derivatives.

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Soret Adrien, Blanco Luis and Deloisy Sandrine, An Unusual and Stereoselective Michael Addition of αAmino Ester-Derived N-Lithiated Azomethine Ylides, Letters in Organic Chemistry 2006; 3 (9) . https://dx.doi.org/10.2174/157017806778700006