Progress in Asymmetric Catalytic Reduction of Diketones

doi:10.6023/cjoc202207045

Abstract

Chiral diols are an integral part of chiral building blocks and synthetic intermediates. Transition metal-catalyzed asymmetric hydrogenation and transfer hydrogenation of diketones are recognized as one of the most straightforward and efficient methods for the preparation of enantiomerically enriched diols. Meanwhile, the mono-reduction product of diketones, chiral hydroxyketones, has wide application in chiral fragment construction as well, among which, desymmetrization of cyclic diketones possesses the capability of establishing multiple chiral centers in one step. In this paper, research progress of asymmetric hydrogenation and transfer hydrogenation of diketone compounds in recent decades is reviewed from the perspective of different substrate types (1,2-/1,3-/1,4-diketones), with emphasis on the influence of coordination mode between substrate and catalyst species on the stereoselectivity. In addition, future challenges and development tendencies in this field are summarized and prospected.

Key words: chiral diols, chiral hydroxyketone, diketones, asymmetric hydrogenation, asymmetric transfer hydrogenation, coordination mode

Cite this article

Yuxuan Zhang, Limin Xu, Yan Lu, Zhaoguo Zhang. Progress in Asymmetric Catalytic Reduction of Diketones[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3221-3239.

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Fig. & Tab. 18

Scheme 1. Dynamic kinetic resolution process in the asymmetric transfer hydrogenation of 1,2-diketones

Scheme 2. Effect of pH on reaction efficiency and selectivity

Scheme 3. Dynamic kinetic resolution process of benzoin in the presence of a base

Scheme 4. Noncovalent interactions in the transition state

Scheme 5. Synthesis of (R,R)-1,2,4,5-diepoxypentane

Scheme 6. Synthesis of (R,R)-BDPBzP

Scheme 7. Synthesis of Epothilone D chiral fragment

Scheme 8. Ru-biphemp-catalyzed asymmetric hydrogenation of acetylacetone

Scheme 9. Ru-biphemp-catalyzed asymmetric hydrogenation of 1,3-diketones with mechanistic investigations

Scheme 10. Ru-SunPhos-catalyzed asymmetric hydrogenation of 3,5-dioxoamides

Scheme 11. Hydrogen bond “activation” of adjacent carbonyls by heteroatoms

Scheme 12. BDPP(Skewphos)-catalyzed synthesis of its counter-configured enantiomer

Scheme 15. Dynamic kinetic resolution-asymmetric transfer hydrogenation of 2-methyl-1,3-diketones

Figure 1. Asymmetric transfer hydrogenation of α,α-disubstituted 1,3-diketones

Scheme 14. Asymmetric hydrogen transfer reaction of 1-Aryl-3- CF3-1,3-diketones

Scheme 15. Hydrogenative desymmetrization and cyclic lactonization of 2,2,5-trisubstituted 1,3-cyclohexanediones

Scheme 16. Hydrogenative desymmetrization of 2,2,5-trisubstituted 1,3-cyclohexanediones

Figure 2. Stabilizing C—H/π interaction between acetylenic ketone and aromatic ring of the catalyst

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