过渡金属不对称催化通过C—O键形成合成手性叔烷基醚的研究进展

doi:10.6023/cjoc202604011

摘要/Abstract

手性叔烷基醚作为一类重要的结构单元, 广泛存在于天然产物、药物分子及具有生物活性的小分子中. 由于含有四取代的碳立体中心, 该类结构的对映选择性的合成具有挑战性. 近年来, 随着新型手性催化剂的发展与反应设计的不断创新, 该类结构的不对称合成取得了突破性进展. 此文从反应类型和过渡金属催化剂种类出发, 系统综述了基于不对称亲核取代反应、烯烃烷氧基化反应、酮环加成/环化反应、C—H键官能化和卡宾O—H插入串联反应等构建C—O键, 实现手性叔烷基醚合成的研究进展, 重点阐述了各类反应的设计思路、催化体系、底物适用范围及机理, 并对该领域目前面临的挑战及未来发展方向进行了展望.

关键词: 不对称催化, 过渡金属催化, 手性叔烷基醚, 四取代碳手性中心, 不对称C—O键构建

Chiral tertiary alkyl ethers are important structural motifs widely found in natural products, drug molecules, and biologically active small molecules. Owing to the presence of sterically congested tetrasubstituted carbon stereocenters, the enantioselective synthesis of chiral tertiary alkyl ethers poses a significant challenge. In recent years, driven with the development of novel chiral catalysts and continuous innovation in reaction design, remarkable advances have been made in the asymmetric construction of such structures via C—O formation. In this review, the advances are summarized based on reaction types and the transition-metal catalysts employed, including asymmetric nucleophilic substitution, olefin alkoxylation, cycloaddition/annulation of ketones, C—H bond functionalization and cascade carbene O—H insertion reaction. The review focuses on the design principles, catalyst systems, substrate scope, and proposed mechanisms of the discussed reactions. Furthermore, current challenges and future directions in the field are discussed.

Key words: asymmetric catalysis, transition-metal catalysis, chiral tertiary alkyl ether, tetrasubstituted carbon stereocenter, asymmetric construction of C—O bond

引用此文

郑浩宇, 李传莹, 周友运. 过渡金属不对称催化通过C—O键形成合成手性叔烷基醚的研究进展[J]. 有机化学, 2026, 46(8): 2892-2925.

Haoyu Zheng, Chuan-Ying Li, You-Yun Zhou. Progress on Transition-Metal-Catalyzed Asymmetric Synthesis of Chiral Tertiary Alkyl Ethers via C—O Bond Formation[J]. Chinese Journal of Organic Chemistry, 2026, 46(8): 2892-2925.

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图/表 40

图1. 含有手性叔烷基醚结构的天然产物和药物分子

Figure 1. Natural products and pharmaceutical molecules containing chiral tertiary ether structures

图式1. 钯催化分子内不对称烯丙基烷基化反应合成手性色满

Scheme 1. Synthesis of chiral chromans by Pd-catalyzed asymmetric intramolecular allylic alkylation

图式2. 金催化分子内烯丙醇的不对称烯丙基取代反应构建手性四取代色满

Scheme 2. Gold-catalyzed intramolecular asymmetric allylic substitution to construct chiral tetrasubstituted chromanones

图式3. 钯/手性磷酸协同催化分子内烯丙醇的不对称烯丙基取代反应构建手性苯并吗啉结构

Scheme 3. Palladium/chiral phosphoric acid synergistic catalysis for intramolecular asymmetric allylic substitution of allylic alcohol to construct chiral benzoxazine structures

图式 4. 双组分催化剂体系催化醇亲核试剂与乙烯基环氧丙烷的不对称烯丙基烷基化反应

Scheme 4. Two-component catalyst system for asymmetric allylic alkylations with alcohol pronucleophiles

图式5. 基于不对称烯丙基取代的脱羧环加成反应构建手性三级乙烯基1,3-二氧环戊烷

Scheme 5. Decarboxylative cycloaddition via asymmetric allylic substitution for the construction of chiral tertiary vinyl 1,3-dioxcy- clopentane

图式6. 钯催化不对称烯丙基环加成反应

Scheme 6. Pd-Catalyzed asymmetric allylic cycloaddition

图式7. 乙烯基碳酸乙烯酯与醇的不对称烯丙基取代实现三级C—O键的对映选择性构建

Scheme 7. Enantioselective construction of tertiary C—O bond via allylic substitution of vinylethylene carbonates with alcohols

图式8. 钯不对称催化合成叔烯丙基芳基醚

Scheme 8. Pd-catalyzed enantioselective synthesis of tertiary allylic aryl ethers

图式9. Pd/硼烷协同催化乙烯基碳酸乙烯酯与二醇的不对称烯丙基醚化反应

Scheme 9. Asymmetric allylic etherification of vinylethylene carbonates with diols via Pd/B cooperative catalysis

图式10. 铜催化醇与外消旋α-叔卤代酰胺的对映汇聚O-烷基化反应

Scheme 10. Copper-catalyzed enantioconvergent O-alkylation of alcohols with racemic α-tertiary haloamides

图式11. 非手性吡啶配体促进的烯烃与醇的手性选择性自由基羟基三氟甲基化

Scheme 11. Achiral pyridine ligand-enabled enantioselective radical oxytrifluoromethylation of alkenes with alcohols

图式12. Cu(I)/手性磷酸协同催化烷基自由基的去对称化反应

Scheme 12. Catalytic desymmetrizing functionalization of alkyl radicals via Cu(I)/CPA cooperative catalysis

图13. 钯不对称催化烯烃的烷氧基芳基化双官能团化反应构建手性叔烷基醚

Scheme 13. Palladium-catalyzed asymmetric alkoxylation-arylation of alkenes for constructing chiral tertiary alkyl ethers

图式14. 钯催化烯烃对映选择性的芳氧基芳基化反应合成手性1,4-苯并二噁烷和色烷

Scheme 14. Synthesis of chiral 1,4-benzodioxanes and chromans by Pd-catalyzed enantioselective aryloxyarylation of alkenes

图式15. 钯/Xu-Phos催化γ-羟基烯烃的对映选择性手芳基烷氧基化反应

Scheme 15. Palladium/Xu-Phos-catalyzed enantioselective arylalkoxylation of γ-hydroxyalkenes

图16. 钯/Xu-Phos 催化γ-羟基烯烃的不对称烷氧基烯基化反应

Scheme 16. Palladium/Xu-Phos-catalyzed enantioselective alkoxyalkenylation of γ-hydroxyalkenes

图式17. 不对称催化未官能化烯烃的分子间碘醚化反应

Scheme 17. Catalytic asymmetric intermolecular iodoetherification of unfunctionalized alkenes

图式18. 钯不对称催化Wacker型环化反应

Scheme 18. Palladium-catalyzed asymmetric Wacker-type cyclization

图式19. 钯不对称催化串联Wacker氧化/Heck反应

Scheme 19. Palladium-catalyzed asymmetric tandem Wacker oxidation/Heck reaction

图式20. 铜催化烯醇的不对称氢烷氧基化反应合成环醚化合物

Scheme 20. Copper-catalyzed enantioselective hydroalkoxylation of alkenols for the synthesis of cyclic ethers

图式 21. 不对称催化酮的杂Diels-Alder反应

Scheme 21. Catalytic asymmetric hetero Diels-Alder reactions of ketones

图式22. 其他配体和过渡金属不对称催化杂Diels-Alder反应

Scheme 22. Other ligands and transition metal-catalyzed asymmetric hetero Diels-Alder reactions

图式23. 不对称烯催化烯丙基硅烷与异靛酮的[3＋2]环化反应

Scheme 23. Catalytic asymmetric [3＋2] annulation of allylsilanes with isatins

图式24. 钯催化对映选择三亚甲基甲烷烯与氟化酮的[3＋2]环加成反应

Scheme 24. Palladium-catalyzed enantioselective [3＋2] cycloaddition of trimethylenemethane and fluorinated ketones

图式25. 钯催化α-三氟甲基碳负离子和酮的不对称[3＋2]环加成反应

Scheme 25. Palladium-catalyzed asymmetric [3＋2] cycloaddition of α-trifluoromethyl carbanions with ketones

图式26. 钯催化的乙烯基环丙烷与异靛酸的手性 [3＋2]环加成反应

Scheme 26. Palladium-catalyzed asymmetric [3＋2] cycloaddition of vinyl cyclopropanes and isatins

图式27. 钯催化的乙烯基环丙烷与氮杂共轭二烯的非对映选择性与对映选择性[3＋2]环加成反应

Scheme 27. Palladium-catalyzed diastereo-and enantioselective [3＋2] cycloaddition of vinylcyclopropanes with azadienes

图式28. 钯催化乙烯基芳基环丙烷(VACPs)与光生烯酮的不对称[3＋2]环加成反应生成四氢呋喃

Scheme 28. Palladium-catalyzed enantioselective [3＋2] cycloaddition of vinylarylcyclopropanes (VACPs) with photogenerated ketenes to tetrahydrofurans

图式29. Rh/Pd接力不对称催化一锅法合成手性叔烷基醚

Scheme 29. Synthesis of chiral tertiary alkyl ethers via one-pot Rh/Pd relay asymmetric catalysis

图式30. 铜催化β-酮酸酯形式上的不对称C—H键苯氧基化反应

Scheme 30. Copper-catalyzed formal enantioselective phenoxylation of C—H bond of β-keto esters

图式31. 钯催化分子内不对称烯丙基C—H氧化合成色满

Scheme 31. Palladium-catalyzed asymmetric intramolecular allylic C—H oxidation for the synthesis of chromans

图式32. 铑/手性磷酸协同催化重氮化合物、醇和亚胺的不对称串联卡宾O—H键插入/Mannich型反应

Scheme 32. Asymmetric tandem carbene O—H insertion/Mannich-type reaction of diazo compounds and alcohols with imines via Rh/chiral phosphoric acid cooperative catalysis

图式33. 不对称催化重氮、醇和亚胺的三组分反应合成手性叔烷基醚

Scheme 33. Asymmetric catalytic three-component reaction of diazo compounds and alcohols with imines to synthesize tertiary alkyl ethers

图式34. 烯炔醛作为卡宾前体与醇和亚胺的不对称三组分反应合成手性叔烷基醚

Scheme 34. Asymmetric three-component reaction of alcohols and imines with enynal as carbene precursor to synthesize chiral tertiary alkyl ethers

图式35. 不对称催化重氮、醇和亚胺的三组分反应合成手性叔烷基醚

Scheme 35. Asymmetric catalytic three-component reaction of diazo compounds and alcohols with aldehydes to synthesize tertiary alkyl ethers

图式36. 布朗斯特酸催化的不对称合成螺色烷-3,3-吲哚酮

Scheme 36. Bronsted acid catalyzed enantioselective assembly of spirochroman-3,3-oxindoles

图式37. 铜(I)/手性双噁唑啉催化芳基重氮乙酸酯与邻酰基或亚胺基苯酚的不对称环化反应

Scheme 37. Cu(I)/chiral bisoxazoline-catalyzed asymmetric annulation of aryldiazoacetates with o-acyl or o-iminyl substituted phenols

图式38. 铑(II)/手性磷酸协同催化邻重氮苯酚与亚胺的不对称Mannich型反应

Scheme 38. Rh(II)/chiral phosphonic acid co-catalyzed asymmetric Mannich-type reaction of ortho-phenol tethered diazo compounds with imines

图式39. 铜不对称催化串联二炔环化/Meinwald重排合成手性叔醚

Scheme 39. Copper-catalyzed asymmetric cascade diyne cyclization/Meinwald rearrangement for the synthesis of chiral tertiary ethers

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