Chemo-enzymatic synthesis of all isomeric 3-phenylserines and -isoserines

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Chemo-enzymatic synthesis of all isomeric 3-phenylserines and -isoserines

Year: 

1990

Source of publication :

Tetrahedron

Authors :

הניג, הלמוט

.

Volume :

Co-Authors: 

Hönig, H., Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 16, A-8010 Graz, Austria
Seufer-Wasserthal, P., Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 16, A-8010 Graz, Austria
Weber, H., Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 16, A-8010 Graz, Austria

From page: 

3841

To page: 

3850

(

Total pages: 

10

)

Link :

Chemo-enzymatic synthesis of all isomeric 3-phenylserines and -isoserines

Abstract: 

The synthesis of all isomers of 3-phenylserines and 3-phenylisoserines in enantiomerically pure form is presented. Diastereomerically pure educts (threo/erythro-2-azido-3-butanoyoxy-3-phenyl-propionic esters, threo/erythro-3-azido-2-butanoyloxy-3-phenylpropionic esters, threo-2-butanoylamino-3-butanoyloxy-3-phenylpropionic ester, erythro-3-butanoylamino-2-butanoyloxy-3-phenyl-propionamide) were prepared from cinnamic acid derivatives or via aldol condensations of benzaldehyde and suitable enolates in few steps. These racemates were resolved with lipases from Candida cylindracea (CC) and Pseudomonas fluorescens (P) and the obtained products were hydrogenated to 3-phenylserines and -isoserines. The influence of the acyl group in the enzymatic resolution of erythro-3-azido-2-acyloxy-3-phenylpropionic esters was investigated. © 1990.