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Synthesis of Valuable Chiral Intermediates by Isolated Ketoreductases: Application in the Synthesis of α‐Alkyl‐β‐hydroxy Ketones and 1,3‐Diols
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2006
Year
Asymmetric CatalysisBiochemistryα‐Alkyl‐β‐hydroxy Ketonesα‐Substituted 1,3‐DiketonesNatural SciencesDiversity-oriented SynthesisOrganic ChemistryNon‐symmetrical DiketonesStereoselective SynthesisChemistryNatural Product SynthesisValuable Chiral IntermediatesSynthetic ChemistryEnantioselective SynthesisIsolated KetoreductasesCorresponding β‐Keto Alcohols
Abstract Regio‐ and stereoselective reductions of α‐substituted 1,3‐diketones to the corresponding β‐keto alcohols or 1,3‐diols by using commercially available ketoreductases (KREDs) are described. A number of α‐monoalkyl‐ or dialkyl‐substituted symmetrical as well as non‐symmetrical diketones were reduced in high optical purities and chemical yields, in one or two enzymatic reduction steps. In most cases, two or even three out of the four possible diastereomers of α‐alkyl‐β‐keto alcohols were synthesized by using different enzymes, and in two examples both ketones were reduced to the 1,3‐diol. By replacing the α‐alkyl substituent with the OAc group, 1‐keto‐2,3‐diols, as well as 1,2,3‐triols were synthesized in high optical purities. These enzymatic reactions provide a simple, highly stereoselective and quantitative method for the synthesis of different diastereomers of valuable chiral synthons from non‐chiral, easily accessible 1,3‐diketones.