Recent Developments in Asymmetric Hydrogenation and Transfer Hydrogenation of Ketones and Imines through Dynamic Kinetic Resolution

Abstract

The transition-metal-catalyzed asymmetric transfer hydrogenation (ATH) and asymmetric hydrogenation (AH) of α- and β-substituted ketone or imine derivatives are efficient methods for accessing chiral alcohols or amines bearing up to three stereogenic centers through a dynamic kinetic resolution (DKR) process. This review provides a summary of recent work in this field, focusing on the development of new catalytic systems and on the extension of these asymmetric reductions to new classes of substrates.

1 Introduction

2 Asymmetric Hydrogenation via Dynamic Kinetic Resolution

2.1 α-Substituted Ketones

2.2. α-Substituted β-Keto Esters and Amides

2.3 α-Substituted β-Keto Phosphonates and Sulfones

2.4 α,α′-Disubstituted Cyclic Ketones

2.5 α,β-Disubstituted Cyclic Ketones

2.6 Imine Derivatives

3 Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution

3.1 α-Substituted β-Diketones and Ketones

3.2 α-Substituted β-Keto Esters, Amides and Phosphonates

3.3 β-Substituted α-Keto Esters and Phosphonates

3.4 β-Substituted γ-Keto Esters

3.5 β-Alkoxy Ketones

3.6 Imine Derivatives

4 Conclusion

Key words

asymmetric hydrogenation - asymmetric transfer hydrogenation - dynamic kinetic resolution - chiral alcohols - chiral amines - ste­reo­selectivity - ketones - imines

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