Institut des Biomolécules Max Mousseron, UMR 5247 Université Montpellier 1-CNRS, Place Eugène Bataillon, 34095 Montpellier cedex 05, France.
Chemistry. 2012 Mar 19;18(12):3773-9. doi: 10.1002/chem.201102885. Epub 2012 Feb 9.
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.
在球磨机中，在碱性条件下进行席夫碱的不对称烷基化反应。事先通过研磨保护的甘氨酸盐酸盐和二苯甲酮亚胺，在没有溶剂的情况下制备甘氨酸的起始席夫碱。然后，在球磨机中，在 KOH 的存在下，将席夫碱与卤代衍生物反应。通过添加来源于金鸡纳碱的手性季铵盐，在相转移催化条件下，反应进行不对称反应，得到高达 75%的优异产率和对映体过量值。因为使用了等摩尔量的起始原料，所以大大简化了纯化过程。
