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

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

Journal Name: Letters in Organic Chemistry

Volume 3 , Issue 9 , 2006

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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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Article Details

VOLUME: 3
ISSUE: 9
Year: 2006
Page: [648 - 653]
Pages: 6
DOI: 10.2174/157017806778700006
Price: $65

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