Progresses in the Application of Kinetic Resolution in Transition Metal Catalyzed Asymmetric (Transfer) Hydrogenation

doi:10.6023/cjoc202303001

Abstract

Kinetic resolution (KR) has long been a popular and classical strategy in organic synthesis to obtain optically active compounds from racemic substrates, and transition metal catalyzed asymmetric (transfer) hydrogenation is a powerful method for the synthesis of chiral compounds with high efficiency and atom economy. Over the years, a large variety of unsaturated compounds bearing different types of chiral centers have been kinetically resolved with great efficiency via asymmetric (transfer) hydrogenation using some well-established chiral transition metal catalysts, and KR has been demonstrated to be a versatile technique in the synthesis of various chiral intermediates for biologically active compounds and natural products. The research progresses in this field are summarized. Moreover, the prospects of further developments are also discussed.

Key words: kinetic resolution, asymmetric hydrogenation, asymmetric transfer hydrogenation, transition metal

Cite this article

Yangyang Chu, Zhaobin Han, Kuiling Ding. Progresses in the Application of Kinetic Resolution in Transition Metal Catalyzed Asymmetric (Transfer) Hydrogenation[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1934-1951.

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Fig. & Tab. 23

Scheme 1. Classical kinetic resolution and selectivity factor, dynamic kinetic resolution and parallel kinetic resolution

Scheme 2. Rh catalyzed kinetic resolution-asymmetric hydrogenation of racemic dehydrodipeptide 1

Scheme 3. Rh catalyzed kinetic resolution-asymmetric (transfer) hydrogenation of racemic Morita-Baylis-Hillman adducts

Scheme 4. Rh catalyzed kinetic resolution-asymmetric hydrogenation of racemic (hetero) aromatic aldehyde-derived MBH adducts

Scheme 5. Rh catalyzed kinetic resolution-asymmetric hydrogenation of racemic α,β-unsaturated sulfoxides

Scheme 6. Rh catalyzed kinetic resolution-asymmetric hydrogenation of racemic α,β-unsaturated phosphane oxides and phosphinate

Scheme 7. Rh catalyzed kinetic resolution-asymmetric hydrogenation of racemic 3,4-disubstituted 1,4,5,6-tetrahydropyridines and 1,4-dihydropyridines

Scheme 8. Ru catalyzed kinetic resolution-asymmetric hydrogenation of racemic allylic alcohols

Scheme 9. Ir catalyzed kinetic resolution-asymmetric hydrogenation of racemic allyl alcohols

Scheme 10. Rh catalyzed kinetic resolution-asymmetric hydrogenation of racemic 1-aryl naphathalenes

Scheme 11. Rh catalyzed kinetic resolution-asymmetric transfer hydrogenation of racemic flavanones

Scheme 12. Rh catalyzed kinetic resolution-asymmetric transfer hydrogenation-deoxygenation of racemic flavanones

Scheme 13. Rh catalyzed kinetic resolution-asymmetric transfer hydrogenation of racemic N-acetyl azaflavanones

Scheme 14. Ru catalyzed kinetic resolution-asymmetric hydrogenation of racemic azaflavanones

Scheme 15. Ru catalyzed kinetic resolution-asymmetric transfer hydrogenation of 3-aryl-1-indanones

Scheme 16. Ir catalyzed kinetic resolution-asymmetric hydrogenation of racemic 5-alkyl-5-hydroxypentanoates

Scheme 17. Ru catalyzed kinetic resolution-asymmetric transfer hydrogenation of racemic ferrocene based compound 35

Scheme 18. Ru catalyzed kinetic resolution-asymmetric transfer hydrogenation of racemic 4-formyl-[2,2]-paracyclophanes

Scheme 19. Rh catalyzed kinetic resolution-asymmetric hydrogenation of racemic imines

Scheme 20. Ti catalyzed kinetic resolution-asymmetric hydrogenation of racemic disubstituted 1-pyrrolines

Scheme 21. Ru catalyzed kinetic resolution-asymmetric hydrogenation of racemic 2,3,3-trisubstituted 3H-indoles

Scheme 22. Mn catalyzed kinetic resolution-asymmetric hydrogenation of racemic 2,3,3-trisubstituted 3H-indoles

Scheme 23. Ni catalyzed kinetic resolution-asymmetric hydrogenation of racemic-[2,2]-paracylophane-derived cyclic N-sulfonylimines

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