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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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Detalles Bibliográficos
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
Descripción
Sumario:[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.