Details

Autor(en) / Beteiligte

• Rubio, Omayra H.
• Fuentes de Arriba, Ángel L.
• Monleón, Laura M.
• Sanz, Francisca
• Simón, Luis
• Alcázar, Victoria
• Morán, Joaquín R.

Titel

Bifunctional organocatalysts based on a carbazole scaffold for the synthesis of the Hajos–Wiechert and Wieland–Miescher ketones

Ist Teil von

• Tetrahedron, 2015-02, Vol.71 (8), p.1297-1303

Ort / Verlag

Elsevier Ltd

Erscheinungsjahr

2015

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Several bifunctional organocatalysts based on a carbazole scaffold containing a chiral amine and a synthetic oxyanion-hole have been synthesized and successfully applied to the synthesis of the Hajos–Wiechert and Wieland–Miescher ketones (up to 99% ee). Both enamine activation and H-bonding donor ability of these catalysts were evaluated by preparing catalysts differing in the nature of the amine [(R,R)-cyclohexanediamine or l-proline], the H-bond donor functional group (sulfonamide or amide) and the number of NH bonds. Modeling studies and an X-ray structure fully support the obtained results. [Display omitted]