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  • Title: Highly enantioselective phase-transfer catalytic alkylation in the preparation of non-natural alpha-amino acids via solid phase synthesis using aldimine linker.
    Author: Park HG, Kim MJ, Park MK, Jung HJ, Lee J, Choi SH, Lee YJ, Jeong BS, Lee JH, Yoo MS, Ku JM, Jew SS.
    Journal: J Org Chem; 2005 Mar 04; 70(5):1904-6. PubMed ID: 15730319.
    Abstract:
    A new Merrifield-resin-derived glycinimine tert-butyl ester (9) was prepared and applied to the enantioselective synthesis of non-natural alpha-amino acids. High enantioselectivities (86 to >99% ee) were accomplished by employing the aldimine linker under phase-transfer alkylation conditions, using 50% aqueous CsOH in toluene/chloroform (7:3) at 0 degrees C in the presence of N-(9-anthracenylmethyl)-O(9)-allylcinchonidium bromide (10 mol %).
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