Abstract:

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.

Key words: Biological active and functionalized group; Optically active butanediol derivative; Asymmetric synthesis; Crystal structure