Selenium promoted synthesis of enantiopure pyrrolidines starting from chiral aminoalcohols
| Autor: | Marcello Tiecco, Lorenzo Testaferri, Claudio Santi, Andrea Temperini, Luana Bagnoli, Francesca Marini, Catalina Scarponi |
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| Rok vydání: | 2007 |
| Předmět: |
Allylic rearrangement
enantiopure pyrrolidines Chemistry Organic Chemistry Triphenyltin hydride Catalysis Pyrrolidine Inorganic Chemistry chiral aminoalcohols chemistry.chemical_compound selenium chemistry Enantiopure drug Nucleophile Tosyl Reagent Electrophile Organic chemistry Physical and Theoretical Chemistry |
| Zdroj: | Tetrahedron: Asymmetry. 18:2758-2767 |
| ISSN: | 0957-4166 |
| Popis: | Starting from commercially available enantiomerically pure aminoalcohols and using simple conversions promoted by organoselenium reagents, several enantiomerically pure substituted pyrrolidines were prepared. After double protections (R)- or (S)-2-phenylglycinols were converted into the β-amino selenides by displacing the tosyl group with phenyl selenolate anions. The phenylseleno group was then substituted by an allyl group by treatment with allyltributyltin and AIBN. The reaction of these allylic derivatives with electrophilic phenylselenium reagents afforded selenium containing pyrrolidines as the result of a 5-exo-trig cyclization. The pyrrolidine derivatives thus obtained were reductively deselenylated with triphenyltin hydride and AIBN. Moreover, the selenides were converted into the selenones, which easily gave substitution with different nucleophiles. Enantiopure 2,5-pyrrolidines containing azido, methylthio, cyano and iodo groups were thus obtained. |
| Databáze: | OpenAIRE |
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