Research Progress on Enantioselective Desymmetrization Reactions Involving Metal Carbenes

doi:10.6023/cjoc202206041

Abstract

Metal carbenes have been widely applied in organic synthesis, and they can undergo a variety of chemical transformations due to their versatile reactivities. In this review, the desymmetrization of C—H insertion reaction, Buchner reaction, Si—H insertion reaction and B—H insertion reaction involving metal carbenes is introduced according to the different reaction types of metal carbenes. Under the catalysis of chiral rhodium, ruthenium and copper catalysts, chiral carbocycles, heterocycles, organosilicons and organoborons can be obtained with high enantioselectivity, which greatly enriches the development of asymmetric synthetic chemistry.

Key words: diazo compounds, metal carbene, desymmetrization, aymmetric synthesis

Cite this article

Ming-Yu Teng, Tao Han, En-He Huang, Long-Wu Ye. Research Progress on Enantioselective Desymmetrization Reactions Involving Metal Carbenes[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3295-3301.

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Fig. & Tab. 16

Scheme 1. Reactions involving metal carbenes from diazo com- pounds

Scheme 2. Synthesis of chiral compounds from enantioselective desymmetrization reactions

Scheme 3. Rh-catalyzed desymmetrization of C—H insertion reaction of diazoacetates

Scheme 4. Rh-catalyzed desymmetrization of C—H insertion reaction of cycloalkyl diazoacetates

Scheme 5. Rh-catalyzed desymmetrization of C—H insertion reaction of α-alkyl-α-diazoesters

Scheme 6. Rh-catalyzed desymmetrization of C—H insertion reaction of α-diazo-β-oxosulfones

Scheme 7. Copper-catalyzed desymmetrization of C—H insertion reaction of meso-oxabicyclo diazoketones

Scheme 8. Copper-catalyzed desymmetrization of C—H insertion reaction of 2-sulfonyl-2-diazoacetamides

Scheme 9. Copper-catalyzed desymmetrization of C—H insertion reaction of α-diazo-β-oxosulfones

Scheme 10. Rh-catalyzed desymmetrization of Buchner reaction of δ,δ-diaryl diazoacetoacetates

Scheme 11. Ru-catalyzed desymmetrization of Buchner reaction of diazoacetamides

Scheme 12. Rh-catalyzed desymmetrization of Buchner reaction of α-cyano-α-diazoacetamides

Scheme 13. Ir-catalyzed desymmetrization of Si—H insertion reaction of diazoacetates

Scheme 14. Ru-catalyzed desymmetrization of Si—H insertion reaction of diazoacetates

Scheme 15. Rh-catalyzed desymmetrization of Si—H insertion reaction of diaryl-diazo compounds

Scheme 16. Cu-catalyzed desymmetrization of B—H insertion reaction of diazo compounds

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