光学纯α-羰基单氟代手性中心构建的研究进展

doi:10.6023/cjoc202603001

摘要/Abstract

含氟有机化合物因其独特的理化性质, 在医药、农药及材料科学等领域具有广泛应用. 其中, 手性α-羰基单氟代化合物因其在调控生物活性与分子构型中的关键作用, 近年来在药物发现领域备受关注. 系统总结了近十年来构建此类结构的主要策略, 从以下三个方面进行阐述: (1)不对称亲电/亲核氟化(直接构建C—F键); (2)含氟砌块参与的不对称C—C键构筑; (3)新兴的自由基与协同催化模式. 此外, 通过深入探讨氟原子的电子效应与立体效应对反应活性及立体选择性的影响, 分析各类反应的底物适用范围与局限性, 以期为含单氟代手性中心化合物的构建提供理性设计思路.

关键词: α-氟酮, 手性中心, 不对称氟化, 含氟砌块

Fluorinated organic compounds, owing to their unique physicochemical properties, have found extensive applications in pivotal fields including pharmaceuticals, agrochemicals, and materials science. Notably, enantiomerically pure α-carbonyl monofluorinated compounds containing chiral centers have garnered considerable attention in drug discovery in recent years, owing to their crucial role in regulating biological activity and modulating molecular configuration. This review systematically summarizes the major synthetic strategies for constructing such structures over the past decade, which are categorized into three aspects: (1) achievement of asymmetric fluorination through C—F bond formation; (2) asymmetric formation of C—C bonds utilizing fluorinated nucleophilic or electrophilic building blocks; (3) emerging radical and synergistic catalysis modes. By critically analyzing the electronic and steric effects of fluorine atoms on reactivity and stereoselectivity, we assess the substrate scope and inherent limitations of existing methodologies, aiming to provide rational design principles for the future synthesis of monofluorinated chiral centers.

Key words: α-fluoroketone, chiral center, asymmetric fluorination, fluorine-containing building

引用此文

金成, 祝鑫, 吴宪姚, 巫辅龙, 王长娟, 廉翔, 吴晶晶, 吴范宏. 光学纯α-羰基单氟代手性中心构建的研究进展[J]. 有机化学, 2026, 46(10): 3904-3932.

Cheng Jin, Xin Zhu, Xianyao Wu, Fulong Wu, Changjuan Wang, Xiang Lian, Jingjing Wu, Fanhong Wu. Research Progress on the Construction of Optically Pure α-Keto Monofluoro Chiral Centers[J]. Chinese Journal of Organic Chemistry, 2026, 46(10): 3904-3932.

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图/表 57

图1. 具有α-羰基单氟代手性中心的药品

Figure 1. Drugs with an α-carbonyl monofluoro chiral center

图式1. 手性多取代吡咯烷的非对映发散氟化

Scheme 1. Diastereodivergent fluorination of chiral multi-substituted pyrrolidines

图式2. 多取代5-吡唑酮的不对称氟化

Scheme 2. Asymmetric fluorination of multi-substituted 5-pyrazolone

图式3. α,α-二烷基醛的对映选择性氟化

Scheme 3. Enantioselective fluorination of α,α-dialkyl aldehydes

图式4. 钴催化对映选择性序列的纳扎罗夫环化反应

Scheme 4. Cobalt-catalyzed enantioselective sequential Nazarov cyclization

图式5. 不对称α-炔基化-α-氟化反应

Scheme 5. Asymmetric α-alkynesylation-α-fluorination reaction

图式6. 富电子氨基脲催化剂进行的对映选择性氟化反应

Scheme 6. Enantioselective fluorination reaction catalyzed by a rich electron semicarbazide catalyst

图式7. 碘催化的β-酮酯不对称氟化

Scheme 7. Iodine-catalyzed asymmetric fluorination of β-keto esters

图式8. 双取代2-萘酚的不对称氟化反应

Scheme 8. Asymmetric fluorination reaction of bisubstituted 2-naphthol

图式9. Cu催化的N-酰基-3,5-二甲基吡唑不对称氟化反应

Scheme 9. Cu-catalyzed asymmetric fluorination reaction of N-acyl-3,5-dimethylpyrazole

图式10. 铑催化的N-酰基吡唑对映选择性α-氟化与α-氯化反应

Scheme 10. Enantioselective α-fluorination and α-chlorination reactions of N-acylpyrazoles catalyzed by rhodium catalysts

图式11. Pd催化的天然酰胺对映选择性迁移氟化反应

Scheme 11. Pd-Catalyzed enantioselective migrative carbofluorination of native amides

图式12. 对映选择性亲核α-氟化反应

Scheme 12. Enantioselective nucleophile α-fluorinated simple ketone method

图式13. 外消旋α-氟代溴代酮与芳基锌试剂的Negishi反应

Scheme 13. Negishi reaction of racemic α-fluorobromodone with the zinc aryl reagent

图式14. 氟烯烃加氢不对称合成氟烷烃

Scheme 14. Asymmetric synthesis of fluorinated alkanes by hydrogenation of fluoroolefins

图式15. 镍(II)催化的α-氟酯对映选择性α-肼化反应

Scheme 15. Nickel(II)-catalyzed enantioselective α-hydrazination of α-fluoroester

图式16. 2,3-丁二烯酸酯与3-氟吲哚酮的不对称迈克尔加成反应

Scheme 16. Asymmetric Michael addition reactions of 2,3-butadienoates with 3-fluorooxindoles

图式17. α-氟代羰基化合物与硝基烯烃的不对称迈克尔加成反应

Scheme 17. Asymmetric Michael additions of α-fluorinated carbonyl compounds with nitroolefin

图式18. 吲哚酮烯醇前体与1,1-二苯磺酰基乙烯的不对称迈克尔加成反应

Scheme 18. Asymmetric Michael addition reaction of 1,1-diphenylsulfonylethylene with enolate precursors

图式19. 氮杂芳烃的催化不对称共轭加成反应

Scheme 19. Catalytic asymmetric conjugate addition reaction of N-heteroarenes hydrocarbons

图式20. 2-氟-1,3-二酮与不饱和噻唑酮的催化不对称反应

Scheme 20. Organocatalytic asymmetric reaction of 2-fluoro-1,3-diketones with unsaturated thiazolones

图式21. 对映选择性串联反应组装氟代色满酮

Scheme 21. Enantioselective tandem reaction for the assembly of fluorinated chromanones

图式22. α-氟代氮杂芳基乙酰胺与α,β-不饱和醛的共轭加成反应

Scheme 22. Addition reaction of α-fluoro-azaaryl acetamide cetamide with α,β-unsaturated aldehydes

图式23. 3-氟氧吲哚与乙烯基双膦酸酯的不对称迈克尔加成反应

Scheme 23. Asymmetric Michael addition of 3-fluorooxindoles to vinyl bisphosphonates

图式24. 2-氟-1,3-二酮与2-羟基硝基苯乙烯的反应

Scheme 24. Reaction between 2-fluoro-1,3-dione and 2-hydroxy nitrostyrene

图式25. (R,R)-ProPhenol催化的不对称Mannich反应

Scheme 25. Asymmetric catalytic Mannich reactions catalyzed by (R,R)-ProPhenol

图式26. α-氟代单硫代丙二酸酯与受保护亚胺的不对称催化加成反应

Scheme 26. Asymmetric organocatalyzed addition reactions of α-fluorinated monothiomalonates to protected imines

图式27. α-氟酮的非对映选择性曼尼希反应

Scheme 27. Diastereoselective Mannich reaction using fluorinated ketones

图式28. 使用阳离子结合催化剂直接催化曼尼希反应

Scheme 28. Direct organocatalysis of the Mannich reaction by using a cationic binding catalyst

图式29. α-氟吲哚酮与N-Dpp亚胺的直接催化不对称曼尼希反应

Scheme 29. Direct catalytic asymmetric Mannich reaction of α-fluoroindolinone with N-Dpp imine

图式30. 通过不对称曼尼希反应合成β-四取代β-氟胺

Scheme 30. Synthesis of β-tetrasubstituted β-fluoroamines via asymmetric Mannich reaction

图式31. 手性脲素催化的不对称曼尼希反应

Scheme 31. Asymmetric Mannich reaction catalyzed by chiral urea

图式32. 手性相转移催化剂催化的不对称曼尼希反应

Scheme 32. Asymmetric Mannich reactions catalyzed by chiral phase transfer catalysts

图式33. 铜催化的不对称脱三氟乙酰基羟醛加成反应

Scheme 33. Copper-catalyzed asymmetric aldol addition via detrifluoroacetylation

图式34. 钯催化α-氟茚酮的不对称芳基化反应

Scheme 34. Palladium-catalyzed asymmetric arylation of α-fluoroindanones

图式35. α-氟代β-羟基羧酸酯的不对称酶法合成

Scheme 35. Asymmetric chemoenzymatic synthesis of α-fluoro-β-hydroxy carboxylic esters

图式36. 钯催化α-吲哚酮与芳基三氟甲磺酸酯非对称分子间的α-芳基化反应

Scheme 36. Asymmetric, intermolecular Pd-catalyzed α-arylation of α-fluorooxindoles with aryl triflates

图式37. Cu(I)/双噁唑啉配体催化的羟醛反应

Scheme 37. Cu(I)/Bis(oxazoline) ligand-catalyzed aldol reaction

图式38. α-氟吲哚酮与烯丙基乙酸酯的不对称烯丙基烷基化反应

Scheme 38. Asymmetric allyl alkylation of α-fluorindole with allyl acetate

图式39. 钯催化脱羧烯丙基烷基化反应

Scheme 39. Palladium-catalyzed decarboxylation allylic alkylation reaction

图式40. 铱、铜催化的烯丙基化反应

Scheme 40. Iridium and copper catalysts react to allylation

图式41. 钯铜催化炔烃与氟烯醇三发散不对称烯丙基烷基化反应

Scheme 41. Three-divergent asymmetric allyl alkylation of alkynes and fluoroenols catalyzed by palladium-copper

图式42. Cu(II)催化不对称1,3-偶极环加成反应

Scheme 42. Cu(II)-catalyzed enantioselective 1,3-dipolar cycloaddition

图式43. 手性叔烷基卤化物的不对称合成方法

Scheme 43. Asymmetric synthesis method of chiral tertiary alkyl halides

图式44. 氟化试剂的铜催化亲核加成反应

Scheme 44. Cu-catalyzed nucleophilic addition reaction of fluorination reagents

图式45. 非环状α-氟-β-酮酯的对映选择性烯丙基烷基化反应

Scheme 45. An enantioselective allylic alkylation of acyclic α-fluoro-β-ketoesters

图式46. Ireland-Claisen重排反应合成α-氟羧酸

Scheme 46. Ireland-Claisen rearrangement reaction for synthesizing α-fluorocarboxylic acids

图式47. 共轭和远端二烯烃的单氟烷基化

Scheme 47. A hydromonofluoroalkylation of conjugated and remote dienes

图式48. 铜催化的多氟芳烃的对映选择性亲核取代反应

Scheme 48. Enantioselective Cu-catalyzed nucleophilic substitutions of polyfluoroarenes

图式49. 立体发散法制备手性α-氟代-γ-丁内酯对映体

Scheme 49. Stereocentric synthesis of chiral α-fluoro-γ-butyrolactones

图式50. CPA催化的去对称化反应

Scheme 50. CPA-catalyzed desymmetrization reaction

图式51. [2＋2＋2]环加成反应构建含氟叔碳手性中心

Scheme 51. [2＋2＋2] cycloaddition reaction for constructing fluorinated tertiary carbon stereocenters

图式52. 脱卤质子化合成手性仲α-氟酮

Scheme 52. Dehalogenative protonation for the synthesis of chiral secondary α-fluoroketones

图式53. 钴催化的单氟代烷基化反应

Scheme 53. Cobalt-catalyzed monofluoroalkylation reaction

图式54. 铜催化非对称Sonogashira偶联反应制备四取代碳立体中心

Scheme 54. Copper-catalyzed asymmetric Sonogashira coupling reaction for the preparation of tetra-substituted carbon stereocenters

图式55. 不对称氟叔自由基氰化反应

Scheme 55. Asymmetric fluoro-tertiary radical cyanidation reaction

图式56. 不对称钴催化构建含氟四取代立体中心

Scheme 56. Asymmetric cobalt catalysis for the construction of quaternary stereogenic centers with fluorine atoms

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