手性2,4-二羟甲基吡咯衍生物的不对称合成

在碱Na2CO3或CH3ONa存在下，芳香醛或脂肪醛与芳香取代的甘氨酸甲酯反应，生成Schiff碱，Schiff碱在有机强碱DBU和金属离子作用下，生成1，3－偶极试剂，并与手性丙烯酸薄荷醇酯原位发生不对称1，3－偶极环加成反应，得手性2，4－二醋基四氢吡咯衍生物；然后，在无水THF中用氢化铝锂还原，得纯的手性2，4－二羟甲基四氢吡咯衍生物，所有二酯基，二羟甲基四氢吡啶衍生物的结构都经过红外光谱，核磁共振，质谱鉴定。

Asymmetric synthesis of 2,4-Dihydroxylmethylpyrrolidine derivatives

In the presence of alkali-sodium carbonate or sodium methoxide titrant, aromatic aldehydes or aliphatic aldehydes reacted with glycine methyl esters substituted by aromatic hydrocarbon and formed Schiff bases. Ten Schiff bases became into 1,3 dipolars under the affection of strong organic alkali DBU. Chiral 2,4 pyrrolindinediester derivatives were synthesized by asymmetric 1,3 dipolar cycloaddition of menthyl acrylate and the Schiff bases were prepared in the presence of metal ion. All of the 2,4 pyrrolindinediester derivatives were reduced with lithium aluminum hydride in anhydrous THF, and ten new chiral 2,4 Dihydroxylmethylpyrrolidine derivatives were found. The structure of the 2,4 pyrrolindinediester derivatives and the 2,4 Dihydroxylmethylpyrrolidine derivatives were identified by IR,MS, 1H NMR and 13 C NMR.