The physiologically active groups such as purine and pyrimidine bases are i
ntroduced to the asymmetric synthesis. The optically pure compounds bearing
purine and pyrimidine bases (5a-5e) were prepared via the asymmetric Micha
el addition reaction of purines and pyrimidines as Michael donators with th
e chiral source 5-(R)-[(1R, 2S, 5R)-menthyloxy]-2(5H)-furanone (3a), which
was prepared from the natural chiral auxiliary(-)-menthol. The synthetic me
thod was studied in derail and the new compounds were identified on the bas
is of their analytical data and spectroscopic data, such as [alpha](D)(20),
IR, UV, H-1 NMR, C-13 NMR and MS. The absolute configuration of 5a was est
ablished by X-ray crystallography. The results provided an efficient synthe
tic route to chiral purines and pyrimidine analogues, and offered chiral so
urces for further research on the physiologically active compounds of chira
l nucleotides.