Asymmetric alkylation of tert-butyl glycinate Schiff base with chiral quaternary ammonium salt under micellar conditions.
[reaction: see text] 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.
Okino
T
T
Department of Chemistry, Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
Takemoto
Y
Y