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

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 ?-amino-?-hydroxy motifs.

SUBMITTER: Franchino A

PROVIDER: S-EPMC4756631 | biostudies-literature | 2016 Jan

REPOSITORIES: biostudies-literature

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

Franchino Allegra A Jakubec Pavol P Dixon Darren J DJ

Organic & biomolecular chemistry 20160101 1

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. ...[more]

PMID: 26510469

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