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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