Transition Metal Catalyzed Asymmetric Hydroboration of Internal Alkenes

doi:10.6023/cjoc202207040

Abstract

Transition metal catalyzed asymmetric hydroboration of alkenes is one of the most powerful methods to prepare chiral organoboronates, which has attracted extensive attention of chemists due to its simple raw materials, high atomic economy, diverse structure of borated products, etc. The transition metal catalyzed enantioselective hydroboration of internal alkenes including strained internal alkene, β-substituted styrenes and internal alkenes bearing a coordinating group is summarized.

Key words: hydroboration, asymmetric catalysis, internal alkene, organoboronate

Cite this article

Houxiang Lu, Bijie Li. Transition Metal Catalyzed Asymmetric Hydroboration of Internal Alkenes[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3167-3182.

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Fig. & Tab. 24

Scheme 1. Ligands of norbornene asymmetric hydroboration in earlier studies

Scheme 2. Asymmetric hydroboration of meso-bicyclic hydrazines

Scheme 3. Effective monodentate ligands of asymmetric hydroboration of meso-bicyclic hydrazines

Scheme 4. Cu catalyzed asymmetric hydroboration of norbornenes

Scheme 5. Rh catalyzed asymmetric hydroboration of cyclopropenes

Scheme 6. Earlier studies of metal catalyzed asymmetric hydroboration of β-substituted styrenes

Scheme 7. Rh catalyzed asymmetric hydroboration of cyclic styrene-type olefins

Scheme 8. Asymmetric hydroboration of β-boronic ester substituted styrenes

Scheme 9. Cu catalyzed asymmetric hydroboration of β-substituted styrenes

Scheme 10. Cu catalyzed asymmetric hydroboration of cinnamaldehydes

Scheme 11. Co catalyzed asymmetric hydroboration of β-substituted styrenes

Scheme 12. Diastereoselective hydroboration of cyclo-olefins directed by coordinating groups

Scheme 13. Amide directed asymmetric hydroboration of distal alkenes

Scheme 14. Asymmetric hydroboration of distal alkenes directed by coordinating group

Scheme 15. Rh catalyzed asymmetric hydroboration of trisubstituted alkenes directed by coordinating groups

Scheme 16. Rh catalyzed asymmetric hydroboration of allyl amides

Scheme 17. Cu catalyzed asymmetric hydroboration of non-activated internal olefins

Scheme 18. Rh catalyzed NHC-borane intramolecular asymmetric hydroboration

Scheme 19. Cu catalyzed asymmetric hydroboration of β-boryl styrene

Scheme 20. Rh catalyzed asymmetric hydroboration of enamides

Scheme 21. Rh catalyzed asymmetric hydroboration of silyl enol ethers

Scheme 22. Co catalyzed asymmetric cascade hydrosilylation-hydroboration of terminal alkynes

Scheme 23. Rh catalyzed asymmetric reversed hydroboration of α,β-unsaturated amides

Scheme 24. Rh catalyzed asymmetric hydroboration of β,β-disubstituted α,β-unsaturated amides

References 24

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