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Asymmetric Alkylation of tert-Butyl Glycinate Schiff Base with Chiral Quaternary Ammonium Salt under Micellar Conditions

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journal contribution
posted on 07.04.2001, 00:00 by Tomotaka Okino, Yoshiji Takemoto
The asymmetric alkylation of the tert-butyl glycinate−benzophenone Schiff base 1 with various arylmethyl bromides catalyzed by O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide (2) proceeded smoothly under micellar conditions (5 equiv of 1 M KOH and 0.4 equiv of Triton X-100) to give the alkylated products in good yields and with good enantioselectivity (72−85% ee), depending on the electrophiles.