Enzymemimetic C-N Bond Formations

Mother Nature is also able to create C-N bonds stereoselectively, for instance, ammonia is added to the double bond of fumaric acid with the help of an aspar-tase of bacterium cadaveris to form (S)-aspartic acid (scheme 24) [65,66]. 

In the eyes of a synthetic chemist this might be called a nitrogen-Michael-ad-dition to the a,P-unsaturated acid moiety as the 1,4-acceptor. Thus, it occurred to us that our favourite auxiliary, the hydrazine SAMP, might be used as a chiral ammonia equivalent in asymmetric hetero Michael additions to enoates. 

Fachbereich Chemie der Philipps-Universitat, Hans-Meerwein-Strasse, D-35043 Marburg/Lahn 

Summary A short linear synthesis of erythronolide is discussed as an exemplary case to demonstrate how changes in the attitude towards new synthetic methods increased the efficiency of natural product synthesis. 

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