多功能光学活性丁二醇衍生物的合成和结构

通过新的合成策略,以手性合成子3和具有生物活性的有机碱类化合物4为反应底物,利用Michael不对称加成反应,合成得到光学纯的5-(R)-［(1R,2S,5R)-(-)-氧基］-4-(R)-(杂环碱基)-2(5H)-呋喃酮(5). 加成物5通过还原反应得到了多功能光学活性的二醇类化合物6,产率为42%~82%,e.e.≥98%. 化合物6的化学结构得到了确认,其立体化学结构和绝对构型经X射线晶体学测定得到了确定.

Syntheses and Structures of Some Functionalized Optically Active Butanediol Derivatives

Through the use of the synthetic strategy outlined in this article,the chiral 5-(R)-［(1R,2S,5R)-(-)-menthyloxy］-4-(R)-(heterocyclic base group)-2(5H)-furanones(5) containing one stereogenic center were obtained via the asymmetric Michael addition reaction of heterocyclic bases with the chiron 3. Adducts 5 were reduced to give the functionalized compounds with optical purity,2-(R)-(heterocyclic base group)-1,4-butanediols(6) in good yields with e.e.≥98%. The chemical structure of compound 6 was readily confirmed by elemental analysis data and spectroscopic data. The proposed structures of optically active compounds 6 were consistent with the stereochemistry and the configurations of their molecules were further confirmed by its X-ray crystallography. These results provided a new synthetic strategy to the functionalized optically active butanediol derivatives. This aim of the present study would be to propose further groundwork for any future applications of the functionalized optically active butanediols to the synthesis of important chiral acyclic nucleoside analogues and organic ligands as well as chiral blockings for synthesizing some supramolecular system and chiral medicines.