Organic Synthesis via Oxidative Cascade Biocatalysis

Abstract

Oxidative cascade biocatalysis enabling multistep enzyme-catalyzed reactions in one pot and utilizing molecular oxygen as a green and cheap oxidant is an emerging tool for selective and sustainable chemical synthesis. In this Account, we summarize several new types of oxidative cascade biocatalysis for the regioselective and mostly enantio­selective transformations recently developed in our laboratory. These cascades offer a green and efficient synthesis of many high-value chiral chemicals in high enantiomeric excesses, such as diols, amino alcohols, hydroxy acids, amino acids, hydroxy ketones, ketones, and lactones.

1 Introduction

2 Asymmetric trans-Dihydroxylation of Alkenes to Vicinal Diols

3 Asymmetric Aminohydroxylation of Alkenes to 1,2-Amino Alcohols

4 Asymmetric Transformation of Alkenes into α-Hydroxy Acids

5 Asymmetric Transformation of Alkenes into α-Amino Acids

6 Oxidative Kinetic Resolution of Vicinal Diols

7 Enantioselective Conversion of Epoxides into α-Hydroxy Ketones

8 Regioselective Oxidation of Alkanes to Ketones

9 Enantioselective Conversion of α,β-Unsaturated Ketones into δ-Lactones and Ketones

10 Conclusion

Key words

biocatalysis - biotransformation - enzyme cascade - cascade reactions - oxidation - whole-cell biocatalysis - asymmetric synthesis - green chemistry

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