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Erosion of Stereochemical Control with Increasing Nucleophilicity: O-Glycosylation at the Diffusion Limit

Nucleophilic substitution reactions of 2-deoxyglycosyl donors indicated that the reactivity of the oxygen nucleophile has a significant impact on stereoselectivity. Employing ethanol as the nucleophile resulted in a 1:1 (α:β) ratio of diastereomers under S(N)1-like reaction conditions. Stereoselecti...

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Detalhes bibliográficos
Main Authors: Beaver, Matthew G., Woerpel, K. A.
Formato: Artigo
Idioma:Inglês
Publicado em: 2010
Assuntos:
Acesso em linha:https://ncbi.nlm.nih.gov/pmc/articles/PMC2838447/
https://ncbi.nlm.nih.gov/pubmed/20108907
https://ncbi.nlm.nih.govhttp://dx.doi.org/10.1021/jo902222a
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