| Autor: |
Marque, Sylvain, Razafimahaléo, Vanessa, Dinut, Aurelia, Grach, Guillaume, Prim, Damien, Moreau, Xavier, Gil, Richard |
| Předmět: |
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| Zdroj: |
New Journal of Chemistry; Sep2013, Vol. 37 Issue 9, p2683-2690, 8p |
| Abstrakt: |
The protonation of 2-pyridylalkylamines (PAA) was investigated through quantum chemical calculations at a DFT level of theory in dichloromethane solution. Two different PAA–H+ species and a dynamic equilibrium between protonated forms were evidenced. The overall geometry of the PAA–H+ promoters is strongly influenced by the nature of the moiety and the absolute configuration of the pseudobenzylic stereocenter. Thus, PAA–H+ complexes were used as organocatalysts in the enantioselective hydroxyalkylation of indole derivatives. The combination of PAA, a strong acid and a soft counter-ion was found to be a mandatory parameter to achieve high yields and selectivities allowing hydroxyalkylation of both N–H and N-protected indoles using a unique catalytic system. [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
| Externí odkaz: |
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