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Synthesis of 4-azaindolines using phase transfer catalysis via an intramolecular Mannich reaction.

A series of bifunctional asymmetric phase-transfer catalysts containing novel fluorine-containing urea groups derived from cinchona alkaloids have been synthesized and successfully applied in the asymmetric intramolecular Mannich reaction. The 4-azaindoline products bearing multiple-substrates were obtained in excellent yield (90-99%), with high enantioselectivity (up to 95%) and diastereoselectivity (up to >99:1).