Diastereoselective Synthesis of α‑Quaternary Aziridine-2-carboxylates via Aza-Corey–Chaykovsky Aziridination of N-tert-Butanesulfinyl Ketimino Esters

A general, scalable, and highly diastereoselective aziridination of N-tert-butanesulfinyl ketimino esters is described. The methodology has been utilized to provide straightforward access to previously unobtainable, biologically relevant α-quaternary amino esters and derivatives starting from readil...

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Published inOrganic letters Vol. 17; no. 22; pp. 5614 - 5617
Main Authors Marsini, Maurice A, Reeves, Jonathan T, Desrosiers, Jean-Nicolas, Herbage, Melissa A, Savoie, Jolaine, Li, Zhibin, Fandrick, Keith R, Sader, C. Avery, McKibben, Bryan, Gao, Donghong A, Cui, Jianwen, Gonnella, Nina C, Lee, Heewon, Wei, Xudong, Roschangar, Frank, Lu, Bruce Z, Senanayake, Chris H
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 20.11.2015
Subjects
Aza Compounds - chemistry
Aziridines - chemical synthesis
Aziridines - chemistry
Catalysis
Esters
Molecular Structure
Stereoisomerism
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Summary:A general, scalable, and highly diastereoselective aziridination of N-tert-butanesulfinyl ketimino esters is described. The methodology has been utilized to provide straightforward access to previously unobtainable, biologically relevant α-quaternary amino esters and derivatives starting from readily available precursors.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02838