Benzyl cinchonidinium chloride

The reaction between ( )-2-bromoalkanoates and potassium phthalimide under solid-liquid phase transfer conditions using either (—)- or (-l-)-l-benzyl-cinchonidinium chloride as a chiral phase transfer catalyst gives optically active 2-phthalimido esters. ... 

Smith and co-workers have taken a different approach to the use of organocatalysis for electrocyclic closure to five-membered ring heterocycles (Scheme 19.11). Condensation of aniline 33 with benzaldehyde in the presence of magnesium sulfate as a dehydrating agent led to an intermediate imine. Exposure of this imine to 10 mol% of 8S,9R)-7V-benzyl cinchonidinium chloride 34 as a phase-transfer catalyst in a mixed solvent of toluene and aqueous potassium carbonate at — 15°C led to indoline 35 in 84% yield and 94% ee. Significantly, this method is not limited to... 

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