Development of ProPhenol Ligands for the Diastereo- and Enantioselective Synthesis of β-Hydroxy-α-amino Esters

[Image: see text] A zinc–ProPhenol-catalyzed direct asymmetric aldol reaction between glycine Schiff bases and aldehydes is reported. The design and synthesis of new ProPhenol ligands bearing 2,5-trans-disubstituted pyrrolidines was essential for the success of this process. The transformation opera...

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Autores principales: Trost, Barry M., Miege, Frédéric
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3985890/
https://www.ncbi.nlm.nih.gov/pubmed/24502188
http://dx.doi.org/10.1021/ja4129394
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author Trost, Barry M.
Miege, Frédéric
author_facet Trost, Barry M.
Miege, Frédéric
author_sort Trost, Barry M.
collection PubMed
description [Image: see text] A zinc–ProPhenol-catalyzed direct asymmetric aldol reaction between glycine Schiff bases and aldehydes is reported. The design and synthesis of new ProPhenol ligands bearing 2,5-trans-disubstituted pyrrolidines was essential for the success of this process. The transformation operates at room temperature and affords syn β-hydroxy-α-amino esters in high yields with good to excellent levels of diastereo- and enantioselectivity.
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spelling pubmed-39858902015-02-06 Development of ProPhenol Ligands for the Diastereo- and Enantioselective Synthesis of β-Hydroxy-α-amino Esters Trost, Barry M. Miege, Frédéric J Am Chem Soc [Image: see text] A zinc–ProPhenol-catalyzed direct asymmetric aldol reaction between glycine Schiff bases and aldehydes is reported. The design and synthesis of new ProPhenol ligands bearing 2,5-trans-disubstituted pyrrolidines was essential for the success of this process. The transformation operates at room temperature and affords syn β-hydroxy-α-amino esters in high yields with good to excellent levels of diastereo- and enantioselectivity. American Chemical Society 2014-02-06 2014-02-26 /pmc/articles/PMC3985890/ /pubmed/24502188 http://dx.doi.org/10.1021/ja4129394 Text en Copyright © 2014 American Chemical Society
spellingShingle Trost, Barry M.
Miege, Frédéric
Development of ProPhenol Ligands for the Diastereo- and Enantioselective Synthesis of β-Hydroxy-α-amino Esters
title Development of ProPhenol Ligands for the Diastereo- and Enantioselective Synthesis of β-Hydroxy-α-amino Esters
title_full Development of ProPhenol Ligands for the Diastereo- and Enantioselective Synthesis of β-Hydroxy-α-amino Esters
title_fullStr Development of ProPhenol Ligands for the Diastereo- and Enantioselective Synthesis of β-Hydroxy-α-amino Esters
title_full_unstemmed Development of ProPhenol Ligands for the Diastereo- and Enantioselective Synthesis of β-Hydroxy-α-amino Esters
title_short Development of ProPhenol Ligands for the Diastereo- and Enantioselective Synthesis of β-Hydroxy-α-amino Esters
title_sort development of prophenol ligands for the diastereo- and enantioselective synthesis of β-hydroxy-α-amino esters
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3985890/
https://www.ncbi.nlm.nih.gov/pubmed/24502188
http://dx.doi.org/10.1021/ja4129394
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AT miegefrederic developmentofprophenolligandsforthediastereoandenantioselectivesynthesisofbhydroxyaaminoesters

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