| Research Abstract |
We have found that the kinetic resolution of allylic alcohols possessing a heteroatom substituent at gamma-position by using the Sharpless reagent proceeds with very large rate differences for the two enantismers. We also found that the kinetic resolution of 2-furanyl alcohols and 2-thienyl alcohols also proceeds efficiently thus providing a general method for preparation of homochiral 2-furanyl alcohols and 2-thienyl alcohols, respectively.
With highly efficient method for preparation of these secondary alcohols in hand, we have devoted our efforts to use these alcohols for preparation of natural products and important intermediates for synthesis of biological importance by using 1,2-diastereoselective induction reactions and use of the reactivity of the heteroatom substituents, and furyl and thienyl moiety. As a result, we have succeeded to prepare alpha-hydroxy carboxylic acids, vinyl epoxides, 1-vinyl-1,2-diols, alpha,beta-dialkoxy aldehydes, and gamma-lactones in chiral forms.
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