Cyclopropylmethylsilanes and alpha-keto aldehydes underwent novel [3+2] cycloaddition reaction to afford 2-silylmethyl substituted tetrahydrofurans in good yields. Relative stereochemistries of the products were dependent on the reaction temperatures, trans- and cis-tetrahydrofurans were obtained stereoselectively at 0 degrees C and at -78 degrees C, respectively.