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AMINO ACID ESTERS AS CHIRAL AUXILIARY GROUPS IN LEWIS ACID CATALYZED REACTIONS OF ELECTRON RICH SILOXYDIENES WITH IMINES

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http://pubman.mpdl.mpg.de/cone/persons/resource/persons98735

Waldmann,  Herbert
Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society;

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Waldmann, H., BRAUN, M., & DRAGER, M. (1990). AMINO ACID ESTERS AS CHIRAL AUXILIARY GROUPS IN LEWIS ACID CATALYZED REACTIONS OF ELECTRON RICH SILOXYDIENES WITH IMINES. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 29(12), 1468-1471. doi:10.1002/anie.199014681.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-6B44-8
Abstract
In the presence of various Lewis acids, the amino acid ester-imines 1 undergo tandem Mannich-Michael reactions and aza-Diels-Alder reactions respectively with the Danishefsky diene 2 and the Brassard diene 3. The products are formed in good yields and high diastereomeric excesses. Cleavage of the chiral auxiliary group-achieved by means of a Curtius rearrangement, by which the alpha-C of the amino acid is converted into an aminal-and subsequent hydrolysis afforded unsaturated lactams such as 4 and enaminones 5, which find use as synthetic building blocks.