Synthesis of a Calixarene-Based Chiral Phase-Transfer Catalyst Derived from Cinchonine and its Application in Asymmetric Alkylation

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The synthesis of a novel calixarene-based chiral phase-transfer catalyst derived from cinchonine has been achieved in four steps from p-t-butylcalix[4]arene. Its catalytic properties were evaluated over a range of conditions by carrying out the phase-transfer alkylation of N-(diphenylmethylene)glycine t-butyl ester with benzyl bromide. Under the optimal conditions the alkylated product was formed in 96% yield with 91% ee.