Three glucosides with long alkyl group, dodecyl-b-D-glucopyranoside (I), dodecyl-a-D-glucopyranoside (II), and sodium 1-b-D-dodecyl glucopyranouronate (III) were synthesized. All these glucosides form micelles in aqueous solution when the concentration is above the individual crit. micellar concentration Reduction of a variety of Ph alkyl ketones which were solubilized in the micelles formed from above glucoside were performed by sodium borohydride. In the micelles of I or II, a different level of optical yield were achieved; one of the most interesting example is for Ph Et ketone in I, the e.e. value is as high as 98%. It can be rationalized that the reduction takes place at interior side of polar layer of micelle by these experimental facts: no reduction for much hydrophobic substrates in any micelle and almost no reduction for all substrates in anionic micelle III. An intermol. neg. hydrogen complex from BH4 and two adjacent glucose moieties of glucoside surfactant was proposed in action of asym. reduction based on the result that the optical yield for I micelle is completely inhibited by addition of a non-ligand surfactant, cetyltrimethylammonium bromide.

Key words: SODIUM COMPOUNDS, MICELLE, SURFACTANTS, BENZENE P, GLUCOSE, GLYCOSIDE, STEREOSELECTIVITY, BORANES, REDUCTION REACTION, MONOKETONE