Direct Catalytic Enantio- and Diastereoselective Ketone Aldol Reactions of Isocyanoacetates**

A catalytic asymmetric aldol addition/cyclization reaction of unactivated ketones with isocyanoacetate pronucleophiles has been developed. A quinine-derived aminophosphine precatalyst and silver oxide were found to be an effective binary catalyst system and promoted the reaction to afford chiral oxa...

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Detalles Bibliográficos
Autores principales: delaCampa, Raquel, Ortín, Irene, Dixon, Darren J
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2015
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4678506/
https://www.ncbi.nlm.nih.gov/pubmed/25735645
http://dx.doi.org/10.1002/anie.201411852
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author delaCampa, Raquel
Ortín, Irene
Dixon, Darren J
author_facet delaCampa, Raquel
Ortín, Irene
Dixon, Darren J
author_sort delaCampa, Raquel
collection PubMed
description A catalytic asymmetric aldol addition/cyclization reaction of unactivated ketones with isocyanoacetate pronucleophiles has been developed. A quinine-derived aminophosphine precatalyst and silver oxide were found to be an effective binary catalyst system and promoted the reaction to afford chiral oxazolines possessing a fully substituted stereocenter with good diastereoselectivities and excellent enantioselectivities.
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spelling pubmed-46785062015-12-22 Direct Catalytic Enantio- and Diastereoselective Ketone Aldol Reactions of Isocyanoacetates** delaCampa, Raquel Ortín, Irene Dixon, Darren J Angew Chem Int Ed Engl Communications A catalytic asymmetric aldol addition/cyclization reaction of unactivated ketones with isocyanoacetate pronucleophiles has been developed. A quinine-derived aminophosphine precatalyst and silver oxide were found to be an effective binary catalyst system and promoted the reaction to afford chiral oxazolines possessing a fully substituted stereocenter with good diastereoselectivities and excellent enantioselectivities. WILEY-VCH Verlag 2015-04-13 2015-03-03 /pmc/articles/PMC4678506/ /pubmed/25735645 http://dx.doi.org/10.1002/anie.201411852 Text en © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. https://creativecommons.org/licenses/by/4.0/ © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
delaCampa, Raquel
Ortín, Irene
Dixon, Darren J
Direct Catalytic Enantio- and Diastereoselective Ketone Aldol Reactions of Isocyanoacetates**
title Direct Catalytic Enantio- and Diastereoselective Ketone Aldol Reactions of Isocyanoacetates**
title_full Direct Catalytic Enantio- and Diastereoselective Ketone Aldol Reactions of Isocyanoacetates**
title_fullStr Direct Catalytic Enantio- and Diastereoselective Ketone Aldol Reactions of Isocyanoacetates**
title_full_unstemmed Direct Catalytic Enantio- and Diastereoselective Ketone Aldol Reactions of Isocyanoacetates**
title_short Direct Catalytic Enantio- and Diastereoselective Ketone Aldol Reactions of Isocyanoacetates**
title_sort direct catalytic enantio- and diastereoselective ketone aldol reactions of isocyanoacetates**
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4678506/
https://www.ncbi.nlm.nih.gov/pubmed/25735645
http://dx.doi.org/10.1002/anie.201411852
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AT ortinirene directcatalyticenantioanddiastereoselectiveketonealdolreactionsofisocyanoacetates
AT dixondarrenj directcatalyticenantioanddiastereoselectiveketonealdolreactionsofisocyanoacetates

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