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

The highly enantio- and diastereoselective aldol reaction of isocyanoacetates catalysed by Ag(2)O 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...

Descripción completa

Detalles Bibliográficos
Autores principales: Franchino, Allegra, Jakubec, Pavol, Dixon, Darren J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4756631/
https://www.ncbi.nlm.nih.gov/pubmed/26510469
http://dx.doi.org/10.1039/c5ob02141c
_version_ 1782416368760520704
author Franchino, Allegra
Jakubec, Pavol
Dixon, Darren J.
author_facet Franchino, Allegra
Jakubec, Pavol
Dixon, Darren J.
author_sort Franchino, Allegra
collection PubMed
description The highly enantio- and diastereoselective aldol reaction of isocyanoacetates catalysed by Ag(2)O 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.
format Online
Article
Text
id pubmed-4756631
institution National Center for Biotechnology Information
language English
publishDate 2015
publisher Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-47566312016-03-03 Enantioselective synthesis of (–)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction Franchino, Allegra Jakubec, Pavol Dixon, Darren J. Org Biomol Chem Chemistry The highly enantio- and diastereoselective aldol reaction of isocyanoacetates catalysed by Ag(2)O 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. Royal Society of Chemistry 2015-01-07 2015-10-29 /pmc/articles/PMC4756631/ /pubmed/26510469 http://dx.doi.org/10.1039/c5ob02141c Text en This journal is © The Royal Society of Chemistry 2015 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Franchino, Allegra
Jakubec, Pavol
Dixon, Darren J.
Enantioselective synthesis of (–)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction
title Enantioselective synthesis of (–)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction
title_full Enantioselective synthesis of (–)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction
title_fullStr Enantioselective synthesis of (–)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction
title_full_unstemmed Enantioselective synthesis of (–)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction
title_short Enantioselective synthesis of (–)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction
title_sort enantioselective synthesis of (–)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4756631/
https://www.ncbi.nlm.nih.gov/pubmed/26510469
http://dx.doi.org/10.1039/c5ob02141c
work_keys_str_mv AT franchinoallegra enantioselectivesynthesisofchloramphenicolviasilvercatalysedasymmetricisocyanoacetatealdolreaction
AT jakubecpavol enantioselectivesynthesisofchloramphenicolviasilvercatalysedasymmetricisocyanoacetatealdolreaction
AT dixondarrenj enantioselectivesynthesisofchloramphenicolviasilvercatalysedasymmetricisocyanoacetatealdolreaction

Ejemplares similares