Formal enantioselective synthesis of (−)-allosamizoline using chiral diamine-catalyzed asymmetric aziridination of cyclic enones
| Autor: | Tanachote Ruengsatra, Yasumasa Hamada, Tetsuhiro Nemoto, Risa Muramoto |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
Ketone 010405 organic chemistry Stereochemistry Organic Chemistry Enantioselective synthesis Total synthesis Aziridine 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound Allosamizoline chemistry Organocatalysis Yield (chemistry) Drug Discovery |
| Zdroj: | Tetrahedron. 72:1991-1997 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2016.02.067 |
| Popis: | We developed a highly effective organocatalytic system for asymmetric aziridination of cyclic enones. Catalytic asymmetric aziridination of 2-cyclopenten-1-one with t-butyl p-toluenesulfonyloxy carbamate proceeded using 20 mol % of (1R,2R)-1,2-diphenylethylenediamine derivative with an N-4,4-dimethylcyclohexyl group 1h, producing chiral aziridine ketone (1R,5R)-4 in 82% yield with 99% ee. Organocatalyst 1h was also an effective catalyst for the asymmetric aziridination of other cyclic enones. The obtained chiral aziridine ketone (1R,5R)-4 could be successfully transformed into the key intermediate for the synthesis of (−)-allosamizoline, demonstrating the utility of this asymmetric aziridination for the synthesis of aminocyclopentitol derivatives. |
| Databáze: | OpenAIRE |
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