Synthesis of Cinchonine Quaternary Ammonium Salts and the Catalysis of Asymmetric Alkylation

Abstract

Abstract: Eleven catalysts bearing a free hydroxyl group were prepared by direct N-alkylation with corresponding substituted benzyl bromides under a reflux condition in good yields(57%—88%). Other 4 catalysts with the chiral secondary alcohol protected by allyl, benzyl, propynyl and benzoyl were synthesized via two steps. The ether group at the phase-transfer catalysts could be approached before or after the N-benzylation reaction. In contrast, the hydroxyl group was changed to benzoic acid ester when the quaternary ammonium salt had been prepared. Fifteen phase-transfer catalysts were gotten, and 5 catalysts of them had never been reported. Then, various catalysts were screened for alkylating reactivity of glycine imine ester. Cinchonine derived catalysts Cn-9 proved to be highly reactive in 93% yield with 91% e.e. value.

Key words: Cinchonine, Quaternary ammonium salt, Phase-transfer catalyst, Asymmetric alkylation

TrendMD:

LI Zhi, LIAN Ming-Ming, MENG Qing-Wei*. Synthesis of Cinchonine Quaternary Ammonium Salts and the Catalysis of Asymmetric Alkylation[J]. Chem. J. Chinese Universities, 2010, 31(8): 1564.

References

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