Recent Advances in Organocatalytic Asymmetric Synthesis of 3,4-Dihydropyran-2-ones and 3,4-Dihydropyridin-2-ones

doi:10.6023/cjoc202010039

Abstract

3,4-Dihydropyranone and 3,4-dihydropyridinone substructures are widely found in a variety of natural products and pharmacologically active molecules, so the efficient synthesis of chiral 3,4-dihydropyranones and 3,4-dihydropyridinones has received more and more attention from pharmaceutical chemists and organic chemists. In recent years, organocatalytic asymmetric reaction has become an efficient synthetic method for the construction of chiral heterocyclic compounds. In this review, the remarkable progress and advances in organocatalytic asymmetric reactions for the synthesis of 3,4-dihydro- pyranones and 3,4-dihydropyridinones from 2003 to 2020 are summarized and discussed based on the different types of organocatalysts and reaction mechanisms.

Key words: organocatalysis, asymmetric catalysis, 3,4-dihydropyranones, 3,4-dihydropyridinones

Cite this article

Huiming Di, Yunting Liu, Yanrong Ma, Xinyue Yang, Hui Jin, Lixin Zhang. Recent Advances in Organocatalytic Asymmetric Synthesis of 3,4-Dihydropyran-2-ones and 3,4-Dihydropyridin-2-ones[J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2228-2248.

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Fig. & Tab. 30

Figure 1. Natural products and biologically active molecules with pyran-2-one and pyridin-2-one motifs

Scheme 1. Chiral isothiourea catalyzed synthesis of 3,4-dihy- dropyran-2-ones and 3,4-dihydropyridin-2-ones

Scheme 2. Reaction mechanism for isothiourea catalyzed [4+2] annulation of carboxylic acid with α,β-unsaturated ketone

Scheme 3. Reaction mechanism for isothiourea catalyzed [3+3] annulation of α,β-unsaturated esters with enamines

Scheme 4. Chiral NHC catalyzed synthesis of 3,4-dihydropyran-2-ones and 3,4-dihydropyridin-2-ones

Scheme 5. Reaction mechanism for NHC catalyzed [4+2] annulation of α-chloro aldehydes with α,β-unsaturated ketones

Scheme 6. Reaction mechanism for NHC catalyzed Michael/Michael/Lactonization cascade reaction of α,β-unsaturated aldehydes and 1,3-dicarbonyl ketone with oxidant

Scheme 7. Reaction mechanism for NHC catalyzed Michael/ Michael/Lactonization cascade reaction of α,β-unsaturated aldehydes and dinitrotoluene derivatives with oxidant

Scheme 8. Reaction mechanism for NHC catalyzed [4+2] annulation of esters and α,β-unsaturated imines

Scheme 9. Reaction mechanism for NHC catalyzed [4+2] annulation of carboxylic acid and aza-o-QM

Scheme 10. Reaction mechanism for ketenes and oxindole derivatives by NHC catalysis

Scheme 11. Reaction mechanism for NHC catalyzed 1,2-addi- tion/Claisen rearrangement/lactonization cascade of ynals and enols

Scheme 12. Reaction mechanism for NHC catalyzed [3+3] annulation of α,β-unsaturated aldehydes and 1,3-dicarbonyl ketone with oxidant

Scheme 13. Reaction of 2-aminoacrylates with α,β-unsaturated aldehydes catalyzed by NHC

Scheme 14. Reaction of α,β-unsaturated aldehydes with 1,3-dicarbonyl compounds catalyzed by NHC

Scheme 15. Reaction of α-bromo α,β-unsaturated aldehydes with 1,3-dicarbonyl compounds catalyzed by bifunctional NHC or normal NHC

Scheme 16. Reaction of α-bromo α,β-unsaturated aldehydes with ketimines catalyzed by NHC

Scheme 17. Reaction mechanism for NHC catalyzed DKR/ lactamization of α-bromo α,β-unsaturated aldehydes with enamines

Scheme 18. Reaction mechanism for NHC catalyzed [3+3] annulation of γ-chloro α,β-unsaturated aldehydes with imines

Scheme 19. Reaction mechanism for NHC catalyzed 1,2-addi- tion/Claisen rearrangement cascade of α,β-unsaturated esters with imines

Scheme 20. Synthesis of 3,4-dihydropyran-2-ones and 3,4-di- hydropyridin-2-ones catalyzed by tertiary amine-H bond donor catalyst

Scheme 21. Reaction of arylacetyl phosphonates with β,γ-unsaturated α-keto esters catalyzed by tertiary amine-thiourea catalyst

Scheme 22. Reaction of β-carbonyl thioesters with β,γ-unsaturated α-keto esters catalyzed by tertiary amine-urea catalyst

Scheme 23. Active sites of azlactone 114 and the reaction transition state of Eq. 36

Scheme 24. Reaction of β-carbonyl aldehydes with substrates 117 catalyzed by chiral squaramide

Scheme 25. Reaction of aldehydes with β,γ-unsaturated-α-keto esters catalyzed by chiral secondary amine

Scheme 26. Reaction mechanism for stereoselective synthesis of 128 by aminocatalysis/oxidation one-pot process

Scheme 27. Reaction of aldehydes with α-keto-α,β-unsaturated esters catalyzed by diarylprolinol silyl ether/HOAc

Scheme 28. Reaction of α,β-unsaturated ketones and α,α-disubstituted aldehydes synergistically catalyzed by chiral secondary amine and tertiary amine-thiourea catalyst

Scheme 29. Reaction of aldehydes with β,γ-unsaturated α-keto esters catalyzed by binaphthyl-modified amino diol catalyst

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有机催化不对称合成3,4-二氢吡喃-2-酮和3,4-二氢吡啶-2-酮衍生物研究进展