ASYMMETRIC-SYNTHESIS OF BICYCLIC AMINO-ACID DERIVATIVES BY AZA-DIELS-ALDER 
REACTIONS IN AQUEOUS-SOLUTION

Waldmann, Herbert; BRAUN, M

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ASYMMETRIC-SYNTHESIS OF BICYCLIC AMINO-ACID DERIVATIVES BY AZA-DIELS-ALDER REACTIONS IN AQUEOUS-SOLUTION

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

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Waldmann, H., & BRAUN, M. (1991). ASYMMETRIC-SYNTHESIS OF BICYCLIC AMINO-ACID DERIVATIVES BY AZA-DIELS-ALDER REACTIONS IN AQUEOUS-SOLUTION. LIEBIGS ANNALEN DER CHEMIE, (10), 1045-1048.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-9ADE-2

Abstract

Derivatives 7-10 and 13-16 of methyl and ethyl 2-azabicyclo[2.2.1]heptane-3-carboxylates are synthesized by Aza-Diels-Alder reactions of chiral iminium ions, formed in situ from glyoxylic acid and chiral amines, with cyclopentadiene. Whereas the heterodienophiles derived from phenylglycinol and esters of sterically more demanding amino acids fail to undergo asymmetric cycloadditions, with alanine methyl ester and (R)-1-phenylethylamine hydrochloride the cycloadducts are formed in yields of 15 and 52%, respectively, reaching de values of up to 90:10 for the exo isomers.