期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 18, 期 12, 页码 3773-3779出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201102885
关键词
amino acids; asymmetric synthesis; solid-state synthesis; phase-transfer catalysis; Schiff bases
资金
- CNRS
- MENRT
- Fondation d'Entreprise EADS
The asymmetric alkylation of Schiff bases under basic conditions in a ball mill was performed. The starting Schiff bases of glycine were prepared beforehand by milling protected glycine hydrochloride and benzophenone imine, in the absence of solvent. The Schiff base was then reacted with a halogenated derivative in a ball mill in the presence of KOH. By adding a chiral ammonium salt derived from cinchonidine, the reaction proceeded asymmetrically under phase-transfer catalysis conditions, giving excellent yields and enantiomeric excesses up to 75?%. Because an equimolar amount of starting material was used, purification was greatly simplified.
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