Synthesis of Chiral 1,5-Diols by Combined Enzyme and Metal Catalysis

Significance

A highly efficient preparation of enantiopure 1,5-diol derivatives is reported. The method combines two known, but very different catalytic processes. On one hand, enzymes convert ‘matched’ epimers of the alcohols into acetates. Concomitantly, a ruthenium catalyst racemizes the ‘unmatched’ alcohols into their ‘matched’ epimers. Therefore, the combination of the reactions permits a 100% theoretical yield of desired chiral product instead of the 50% maximum yield expected for a classic kinetic resolution.