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

doi:10.6023/cjoc202010039

摘要/Abstract

3,4-二氢吡喃-2-酮和3,4-二氢吡啶-2-酮结构广泛存在于多种天然产物和具有药理活性的分子中, 因此高效合成手性3,4-二氢吡喃-2酮和3,4-二氢吡啶-2酮受到越来越多药物化学和有机化学研究者的关注. 近年来有机小分子催化的不对称反应已成为构建手性杂环化合物的有效方法. 综述了自2003年至今有机小分子催化的不对称反应合成手性3,4-二氢吡喃酮和3,4-二氢吡啶酮衍生物的研究进展, 并根据不同的催化剂类型及反应机理进行分类讨论.

关键词: 有机催化, 不对称催化, 3,4-二氢吡喃酮, 3,4-二氢吡啶酮

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

引用此文

底慧明, 刘云婷, 马艳榕, 杨鑫悦, 金辉, 张立新. 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[J]. 有机化学, 2021, 41(6): 2228-2248.

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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图/表 30

图1. 含有3,4-二氢吡喃-2-酮和3,4-二氢吡啶-2-酮骨架的天然产物及生物活性分子

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

图式1. 手性异硫脲催化合成3,4-二氢吡喃-2-酮和3,4-二氢吡啶-2-酮

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

图式2. 异硫脲催化羧酸与α,β-不饱和酮的[4+2]环化反应机理

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

图式3. 异硫脲催化α,β-不饱和酯与烯胺的[3+3]环化反应机理

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

图式4. 手性NHC催化合成3,4-二氢吡喃-2-酮和3,4-二氢吡啶-2-酮

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

图式5. NHC催化α-氯醛与α,β-不饱和酮的[4+2]环化反应机理

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

图式6. 氧化剂参与的NHC催化α,β-不饱和醛与1,3-二羰基酮的Michael/Michael/Lactonization串联反应机理

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

图式7. 氧化剂参与的NHC催化α,β-不饱和醛与二硝基甲苯衍生物的Michael/Michael/Lactonization串联反应机理

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

图式8. NHC催化酯与α,β-不饱和亚胺的[4+2]环化反应机理

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

图式9. NHC催化羧酸与aza-o-QM的[4+2]环化反应机理

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

图式10. NHC催化烯酮与氧吲哚衍生物的反应机理

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

图式11. NHC催化炔醛与烯醇的1,2-加成/Claisen重排/内酯化串联反应机理

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

图式12. 氧化剂参与的NHC催化α,β-不饱和醛与1,3-二羰基化合物的[3+3]环化反应机理

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

图式13. NHC催化2-氨基丙烯酸乙酯与α,β-不饱和醛的反应

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

图式14. NHC催化α,β-不饱和醛与1,3-二羰基化合物的反应

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

图式15. 双功能NHC或普通NHC催化α-溴代α,β-不饱和醛与1,3-二羰基化合物的反应

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

图式16. NHC催化α-溴代α,β-不饱和醛与酮亚胺的反应

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

图式17. NHC催化α-溴代α,β-不饱和醛与烯胺的DKR/内酰胺化反应机理

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

图式18. NHC催化γ-氯代α,β-不饱和醛与酮亚胺的环化反应机理

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

图式19. NHC催化α,β-不饱和酯与酮亚胺的1,2-加成/Claisen重排串联反应机理

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

图式20. 叔胺-氢键供体催化剂催化合成3,4-二氢吡喃-2-酮和3,4-二氢吡啶-2-酮

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

图式21. 叔胺-硫脲催化剂催化芳基乙酰磷酸酯与β,γ-不饱和-α-酮酸酯的反应

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

图式22. 叔胺-脲催化剂催化β-羰基硫酯与β,γ-不饱和-α-酮酸酯的反应

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

图式23. 噁唑酮114的活性位点及Eq. 36的反应过渡态

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

图式24. 手性方酰胺催化β-羰基醛与底物117的反应

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

图式25. 手性仲胺催化醛与β,γ-不饱和-α-酮酸酯的反应

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

图式26. 手性胺催化/氧化一锅法不对称合成128的反应机理

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

图式27. 二芳基脯氨醇硅醚/醋酸催化醛与α-酮基-α,β-不饱和酯的反应

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

图式28. 手性仲胺和叔胺-硫脲协同催化α,β-不饱和酮与α,α-双取代醛的反应

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

图式29. 基于联二萘结构的手性氨基二醇催化醛与β,γ-不饱和-α-酮酸酯的反应

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

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