几种4-取代-L-脯氨酸衍生物的合成

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.

Synthesis of several 4-substituted-L-proline derivatives

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.