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几种4-取代-L-脯氨酸衍生物的合成
引用本文:陈策,王舟,毛宇鸿,马银辉,王伟.几种4-取代-L-脯氨酸衍生物的合成[J].化学研究,2013(2):111-114.
作者姓名:陈策  王舟  毛宇鸿  马银辉  王伟
作者单位:陕西师范大学化学化工学院
基金项目:陕西省自然科学基金资助项目(2011JM2001)
摘    要:以Boc-(4R)-羟基-(2S)-脯氨酸为原料,在NaH作用下与苄位溴代试剂发生醚化反应,合成了几种4-取代-L-脯氨酸类手性催化剂,即在(4R)-羟基-(2S)-脯氨酸的4-位上引入不同的苄氧基以期提高其催化活性和脂溶性,并通过1 H NMR、13 C NMR和HRMS对合成产物的结构进行表征,确定其为目标产物.实验结果还表明,当苯环上连有强的吸电子基团时反应很难进行,而当连有给电子基团时反应相对较容易进行且反应条件较温和.

关 键 词:4-取代-L-脯氨酸衍生物  Boc-(4R)-羟基-(2S)-脯氨酸  手性催化剂  合成

Synthesis of several 4-substituted-L-proline derivatives
CHEN Ce,WANG Zhou,MAO Yu-hong,MA Yin-hui,WANG Wei.Synthesis of several 4-substituted-L-proline derivatives[J].Chemical Research,2013(2):111-114.
Authors:CHEN Ce  WANG Zhou  MAO Yu-hong  MA Yin-hui  WANG Wei
Institution:*(College of Chemistry and Chemical Engineering,Shaanxi Normal University,Xi’an 710062,Shaanxi,China)
Abstract:In order to improve the liposolubility of chiral catalysts and increase their enantiose- lectivity, several chiral catalysts of 4-suhstituted-L-proline derivatives were designed and syn- thesized from Boc-(4R)-hydroxy-(2S)-proline, which was treated with Nail in anhydrous tet- rahydrofuran and followed by etherification with ARCH2 Br to form final products. The final products were then characterized by 1H NMR,laC NMR and HRMS and confirmed as the tar- get product. The experiment results also showed that the reaction hardly proceeded as the ben- zene ring is linked with an electron-withdrawing group, whereas the reaction proceeded easily if the benzene ring is linked with an electron-donating group and the reaction conditions in this case can be more moderate.
Keywords:4-substituted-L-proline derivatives  Boc- ( 4R )-hydroxy- ( 2S)-proline  chiral cata- lysts  synthesis
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