Abstract
Enantiodifferentiating transformation of a prochiral hydroxyl group of polyols possessing σ-symmetry provides versatile chiral building blocks which can be incorporated into diverse target structures. We have developed nonenzymatic methods which are applicable to a variety of prochiral diols and triols by utilizing l- or d-menthone as chiral template. Thus, 2-substituted 1, 3-propanediols and meso-1, 2-, 1, 3-, and 1, 4-diols are enantiodifferentiatingly functionalized by utilizing a highly stereoselective ring-cleavage reaction of spiroacetal derived from l-menthone. A stereoselective synthesis of meso-1, 3, 5-pentanetriols and their enantioselective transformation by the reaction with l-menthone are also described.
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