Enantioselective synthesis of (?)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction?

Organic & Biomolecular Chemistry Pub Date: 2015-10-29 DOI: 10.1039/C5OB02141C

Abstract

The highly enantio- and diastereoselective aldol reaction of isocyanoacetates catalysed by Ag2O and cinchona-derived amino phosphines applied to the synthesis of (?)- and (+)-chloramphenicol is described. The concise synthesis showcases the utility of this catalytic asymmetric methodology for the preparation of bioactive compounds possessing α-amino-β-hydroxy motifs.

Graphical abstract: Enantioselective synthesis of (?)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction
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