The functionalized spiro-cyclopropane derivatives 4 containing four stereogenic centers were obtained in good yields with d.e≥98% via tandem double Michael addition/internal nucleophilic substitution of the onvel chiral synthon 1. 4-was undergone regioselective transformation of the auxiliary goup under presence of acetone/5% HCl to afford single hydrolytic products 5 in yields of 50%～78% with d.e. .≥98% and also to afford single alcoholic products 6 in yields of 50% ～78% with d.e.≥98% under presence of CH3OH/p-TsOH. The novel chiral compounds 5a～5f and 6a～6e were identified on the basis of their analytical data and spectroscopic data, such as UV, IR, 1^H NMR, 13^C NMR, MS elementary analysis and X-ray crystallography.

Key words: SPIRO COMPOUNDS, CYCLOPROPANE, SELECTIVITY, NUCLEOPHILIC REACTION, SUBSTITUTION REACTION, MICHAEL ADDITION REACTION, ELEMENTAL ANALYSIS