Research Progress on Asymmetric Synthesis of Flavanones

doi:10.6023/cjoc202109030

Abstract

Flavanones and their derivatives are important bioactivenatural products. The skeleton structure exists in many complex natural products and has a wide range of biological activities. The research on flavanones is getting more and more attention. Chiral flavanone itself is an important chemical substance in plants and has potential medicinal value, but its content is small. Many chemists are committed to solve the problem through synthetic methods, which promotes the preparation of enantiomerically enriched flavanones. The preparation process has certain limitations, but for some complex structures of flavanone compounds it is still difficult to achieve, This is going to be a problem to overcome in the future. The asymmetric synthesis methods of flavanones are reviewed in recent years. The synthesis methods include carbonyl reduction and chiral resolution of raceme, formation of carbon-carbon bonds, formation of carbon-heterobonds and other types of synthesis methods.

Key words: flavanones, asymmetric synthesis, review

Cite this article

Lihua Wang, Xushun Gong, Ting Lei, Shizhi Jiang. Research Progress on Asymmetric Synthesis of Flavanones[J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 758-769.

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Fig. & Tab. 30

Scheme 1. Ruthenium-catalyzed asymmetric hydrogenation of flavonoids 1

Scheme 2. Resolution of racemic flavanone 4 with L-(+)-2,3-butanedithiol

Scheme 3. Flavanone compound 4 resolved by converting into cis-amine compounds 6a and 6b

Scheme 4. Rhodium-catalyzed nonenzymatic kinetic resolution of racemic flavanone derivatives

Scheme 5. Enzymatic kinetic resolution of racemic flavanol ester 8

Scheme 6. Enzymatic kinetic resolution of racemic flavanone oxime acetate 9

Scheme 7. Mitsunobu reaction combined with enzymatic resolution to generate enantiomerically enriched flavanone enantiomers

Scheme 8. Synthesis of chiral flavanones by conjugate addition using chiral sulfoxide structure

Scheme 9. Rhodium catalyzed asymmetric 1,4-addition reactions of chromone with sodium tetraarylborate in the presence of C2 chiral disulfone ligand

Scheme 10. Rh-catalyzed enantioselective 1,4-addition of arylboronic acids to chromenones 18

Scheme 11. Rhodium-catalyzed asymmetric conjugate addition of arylboronic acid to chromone

Scheme 12. Rhodium-catalyzed asymmetric 1,4-addition reaction of chromone and phenylboronic acid

Scheme 13. Rhodium-catalyzed asymmetric 1,4-addition reaction of arylboronic acid and chromone

Scheme 14. Pd/PyOX catalyzed the asymmetric conjugate addition reaction of aryl boronic acid and chromone

Scheme 15. Asymmetric 1,4-addition of phenylboronic acid and chromone catalyzed by ligand 1,10-phenanthroline

Scheme 16. Enantioselective synthesis of flavanone catalyzed by chiral thiourea

Scheme 17. Ni (29)-catalyzed asymmetric intramolecular Oxa- Michael addition reaction of α,β-unsaturated ketones

Scheme 18. Asymmetric intramolecular oxa-Michael addition reaction of α,β-unsaturated ketones catalyzed by chiral N-trifluorophosphoramide

Scheme 19. Oxa-Michael addition/decarboxylation reaction catalyzed by bifunctional cinchona alkaloid

Scheme 20. Cinchona alkaloid catalyzed the asymmetric cycli- zation of 2,6-dihydroxychalcone 32

Scheme 21. Asymmetric ion pair catalysis for the reversible cyclization of 2-hydroxychalcone to flavanone

Scheme 22. Synthesis of flavanones by enantioselective bionic cyclization of 2-hydroxychalcone

Scheme 23. Bionic chalcone cyclization reaction

Scheme 24. S-Ttriazine-catalyzed asymmetric cyclization of 2-hydroxychalcone

Scheme 25. Synthesis of (S)-(–)-pinostrobin by Mitsunobu method

Scheme 26. Synthesis of (S)-(-)-pinostrobin by Mitsunobu method

Scheme 27. Bifunctional cinchona alkaloids catalyze tandem intramolecular oxa-Michael addition/electrophilic fluorination reaction

Scheme 28. Intramolecular oxa-Michael addition/electrophilic halogenation tandem reaction

Scheme 29. Enantioselective tandem reaction of MBH carbonate and benzylamine

Scheme 30. Stereoselective synthesis of flavanones by intramolecular benzoin reaction

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