Synthesis of Novel Chiral Phase Transfer Catalysts and Their Applications in Asymmetric Phase Transfer Catalytic Reactions

Herein a serial of novel chiral phase transfer catalysts derived from cinchona alkaloids, containing a 8-member cycle, have been synthesized. The serial of catalysts have been applied to the asymmetric alkylation reaction and the asymmetric Darzens Reaction with a serial of satisfying and interesting results including moderate to excellent ee values (63-99.7%) in the asymmetric alkylation reactions and high diastereos selection and low to moderate ee values in the asymmetric Darzens Reaction (2.23:1 to trans only). An interesting phenomenon of asymmetric Darzens Reaction has also been discovered and explored, which probably concerning to the conjugation effect. A novel reasonable mechanism has also been put forward to explain this interesting phenomenon.