Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation

Autor:	Zhenquan Sun, Andrew G. Dalling, Cécile S. Le Duff, Benjamin R. Buckley, Louise Male, John S. Fossey, William D. G. Brittain
Jazyk:	angličtina
Rok vydání:	2019
Předmět:	Triazole chemistry.chemical_element Alkyne lcsh:Medicine Synthetic chemistry methodology 010402 general chemistry 01 natural sciences Medicinal chemistry Article Catalysis Kinetic resolution chemistry.chemical_compound Stereochemistry Asymmetric catalysis lcsh:Science chemistry.chemical_classification Multidisciplinary 010405 organic chemistry lcsh:R Diastereomer Substrate (chemistry) Homogeneous catalysis Copper 0104 chemical sciences Chemistry chemistry lcsh:Q Azide
Zdroj:	Scientific Reports, Vol 9, Iss 1, Pp 1-9 (2019) Scientific Reports
ISSN:	2045-2322
DOI:	10.1038/s41598-019-50940-4
Popis:	A non-enzymatic simultaneous (coined coetaneous) kinetic resolution of a racemic alkyne and racemic azide, utilising an asymmetric CuAAC reaction is reported. The use of a CuCl (R,R)-Ph-Pybox catalyst system effects a simultaneous kinetic resolution of two racemic starting materials to give one major triazolic diastereoisomer in the ratio 74:12:4:10 (dr 84:16, 90% ee maj). The corresponding control reaction using an achiral copper catalyst gives the four possible diastereoisomers in a 23:27:23:27 ratio, demonstrating minimal inherent substrate control.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::7c9bcd197cefdde4cc03fbe0f4689ff5 http://link.springer.com/article/10.1038/s41598-019-50940-4 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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