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

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

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Title: Asymmetric Mannich Synthesis of α-Amino Esters by Anion-Binding Catalysis
Author: Wasa, Masayuki; Liu, Richard Y.; Roche, Stéphane P.; Jacobsen, Eric N.

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Citation: Wasa, Masayuki, Richard Y. Liu, Stéphane P. Roche, and Eric N. Jacobsen. 2014. “Asymmetric Mannich Synthesis of α-Amino Esters by Anion-Binding Catalysis.” Journal of the American Chemical Society 136 (37): 12872-12875. doi:10.1021/ja5075163. http://dx.doi.org/10.1021/ja5075163.
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Abstract: 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.
Published Version: doi:10.1021/ja5075163
Other Sources: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4183616/pdf/
Terms of Use: This article is made available under the terms and conditions applicable to Other Posted Material, as set forth at http://nrs.harvard.edu/urn-3:HUL.InstRepos:dash.current.terms-of-use#LAA
Citable link to this page: http://nrs.harvard.edu/urn-3:HUL.InstRepos:22856916
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