Recent Advances in Catalytic Asymmetric Synthesis of Chiral 1,2-Bis(boronic) Esters

doi:10.6023/cjoc202312014

Abstract

Chiral 1,2-bis(boronic) esters are essential building blocks in the field of synthetic chemistry, and their catalytic asymmetric synthesis has attracted significant interest of chemists. Recently, asymmetric diboration of olefins, using transition metals and chiral diols, has emerged as the straightforward and atom-economical methods for producing highly valuable chiral 1,2-bis(boronic) esters. Asymmetric hydrogenation of vinyl bis(boronic) esters can be a complementary approach to asymmetric diboration for synthesizing these products. Additionally, borofunctionalization of alkenes or alkynes represents another effective strategy for constructing these highly valuable scaffolds. A recent innovation involves catalytic asymmetric migratory coupling reactions with gem-diborylalkanes, offering new avenues for synthesizing chiral 1,2-bis(boronic) esters. The latest developements and challenges in synthesizing these moleculeshis are summarized, and the potential future research directions in this field are prospected.

Key words: chiral 1,2-bis(boronic) esters, diborylation, hydroboration, borofunctionalization, gem-diborylalkanes, migratory coupling reactions

Cite this article

Chonglei Ji, Dewei Gao. Recent Advances in Catalytic Asymmetric Synthesis of Chiral 1,2-Bis(boronic) Esters[J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1385-1402.

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Fig. & Tab. 18

Figure 1. Synthetic potential of 1,2-bis(boronic) esters and the methods used to prepare these privileged scaffolds

Figure 2. Rhodium-catalyzed enantioselective diboration of alkenes

Figure 3. Enantioselective diboration of simple alkenes: reaction development and substrate scope

Figure 4. Rhodium-catalyzed enantioselective diboration of terminal alkenes

Figure 5. Pd-catalyzed enantioselective diboration of prochiral allenes

Figure 6. Palladium-catalyzed asymmetric diboration of allenes and subsequent transformations

Figure 7. Pt-catalyzed enantioselective diboration of terminal alkenes

Figure 8. Pt-catalyzed enantioselective diboration of 1,3-dienes

Figure 9. Pt-catalyzed enantioselective diboration of vinyl boronic esters

Figure 10. Pt-catalyzed stereoselective diboration of spirocyclobutenes

Figure 11. Carbohydrate-catalyzed enantioselective diboration of alkenes

Figure 12. Cu-catalyzed stereoselective diboration of alkenes and alkynes

Figure 13. Cu-catalyzed borofunctionalization of alkenes

Figure 14. Cu-catalyzed tandem borylation/1,2-addition

Figure 15. Cu-catalyzed enantioselective diboration of 1?chloro-1-trifluoromethylalkenes

Figure 16. Catalytic enantioselective hydrogenation of vinyl bis(boronates)

Figure 17. Our idea to construct chiral 1,2-bis(boronic) esters featuring acyclic, 1,3-stereocenters

Figure 18. Asymmetric synthesis of chiral 1,2-bis(boronic) esters featuring acyclic, 1,3-stereocenters

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