Asymmetric Mannich Synthesis of α-Amino Esters by Anion-Binding Catalysis

[Image: see text] We report a scalable, one-pot Mannich route to enantioenriched α-amino esters by direct reaction of α-chloroglycine ester as a practical imino ester surrogate. The reaction is promoted by a chiral aminothiourea, which is proposed to operate cooperatively by generating an iminium io...

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Autores principales: Wasa, Masayuki, Liu, Richard Y., Roche, Stéphane P., Jacobsen, Eric N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4183616/
https://www.ncbi.nlm.nih.gov/pubmed/25178040
http://dx.doi.org/10.1021/ja5075163
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author Wasa, Masayuki
Liu, Richard Y.
Roche, Stéphane P.
Jacobsen, Eric N.
author_facet Wasa, Masayuki
Liu, Richard Y.
Roche, Stéphane P.
Jacobsen, Eric N.
author_sort Wasa, Masayuki
collection PubMed
description [Image: see text] We report a scalable, one-pot Mannich route to enantioenriched α-amino esters by direct reaction of α-chloroglycine ester as a practical imino ester surrogate. The reaction is promoted by a chiral aminothiourea, which is proposed to operate cooperatively by generating an iminium ion by chloride abstraction and an enolate by deprotonation, followed by highly stereoselective C–C bond formation between both reactive intermediates associated non-covalently within the catalyst framework.
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spelling pubmed-41836162015-09-01 Asymmetric Mannich Synthesis of α-Amino Esters by Anion-Binding Catalysis Wasa, Masayuki Liu, Richard Y. Roche, Stéphane P. Jacobsen, Eric N. J Am Chem Soc [Image: see text] We report a scalable, one-pot Mannich route to enantioenriched α-amino esters by direct reaction of α-chloroglycine ester as a practical imino ester surrogate. The reaction is promoted by a chiral aminothiourea, which is proposed to operate cooperatively by generating an iminium ion by chloride abstraction and an enolate by deprotonation, followed by highly stereoselective C–C bond formation between both reactive intermediates associated non-covalently within the catalyst framework. American Chemical Society 2014-09-01 2014-09-17 /pmc/articles/PMC4183616/ /pubmed/25178040 http://dx.doi.org/10.1021/ja5075163 Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Wasa, Masayuki
Liu, Richard Y.
Roche, Stéphane P.
Jacobsen, Eric N.
Asymmetric Mannich Synthesis of α-Amino Esters by Anion-Binding Catalysis
title Asymmetric Mannich Synthesis of α-Amino Esters by Anion-Binding Catalysis
title_full Asymmetric Mannich Synthesis of α-Amino Esters by Anion-Binding Catalysis
title_fullStr Asymmetric Mannich Synthesis of α-Amino Esters by Anion-Binding Catalysis
title_full_unstemmed Asymmetric Mannich Synthesis of α-Amino Esters by Anion-Binding Catalysis
title_short Asymmetric Mannich Synthesis of α-Amino Esters by Anion-Binding Catalysis
title_sort asymmetric mannich synthesis of α-amino esters by anion-binding catalysis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4183616/
https://www.ncbi.nlm.nih.gov/pubmed/25178040
http://dx.doi.org/10.1021/ja5075163
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AT rochestephanep asymmetricmannichsynthesisofaaminoestersbyanionbindingcatalysis
AT jacobsenericn asymmetricmannichsynthesisofaaminoestersbyanionbindingcatalysis

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