α-手性三级叠氮化合物的不对称催化合成新进展★

doi:10.6023/A23070359

化学学报 ›› 2023, Vol. 81 ›› Issue (11): 1590-1608.DOI: 10.6023/A23070359 上一篇下一篇

所属专题：庆祝《化学学报》创刊90周年合辑

综述

α-手性三级叠氮化合物的不对称催化合成新进展^★

高杨^a, 张学鑫^a, 余金生^a^,^*(), 周剑^a^,^b^,^c^,^*()

a 华东师范大学化学与分子工程学院石油化工分子转化与反应工程全国重点实验室上海分子治疗与新药创制工程技术研究中心上海市绿色化学与化工过程绿色化重点实验室上海 200062
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032
c 海南师范大学热带药用资源化学教育部重点实验室海口 571127

投稿日期:2023-07-28 发布日期:2023-09-30

作者简介:

高杨, 女, 汉族, 1996年出生于甘肃金昌. 2016年9月本科毕业于河西学院, 2019年9月硕士毕业于云南民族大学有机化学专业, 随后加入华东师范大学周剑教授课题组攻读博士学位, 研究方向为有机小分子催化构建α-手性三级叠氮化合物.

张学鑫, 男, 汉族, 1992年出生于甘肃张掖. 2016年9月本科毕业于河西学院, 2019年9月硕士毕业于云南民族大学有机化学专业, 随后加入华东师范大学周剑教授课题组攻读博士学位, 研究方向为手性有机硅化合物的合成.

余金生, 华东师范大学化学与分子工程学院教授, 博士生导师. 2011年本科毕业于江西师范大学; 2016年博士毕业于华东师范大学, 导师周剑教授; 2017至2019年获JSPS资助在日本微生物化学研究所从事博士后研究, 导师Masakatsu Shibasaki教授. 2019年2月加入华东师范大学开展研究工作, 主要从事有机氟硅化学和绿色农药创制等研究.

周剑, 华东师范大学化学与分子工程学院教授, 博士生导师. 本科毕业于四川师范大学; 2004年毕业于中科院上海有机所, 获理学博士学位, 导师唐勇研究员; 先后在日本东京大学Shu Kobayashi和德国马普煤炭研究所Benjamin List课题组从事博士后研究后, 于2008年底加入华东师范大学. 研究兴趣在于立足协同催化的理念, 结合新催化剂和新试剂的设计开发, 发展导向具有手性季碳的药物优势骨架的不对称催化构建新方法.

^★庆祝《化学学报》创刊90周年.

基金资助:
国家自然科学基金(21971067); 国家自然科学基金(22171087); 上海市教育委员会科研创新计划(2023ZKZD37); 上海市科技创新行动计划(20JC1416900); 上海市科技创新行动计划(21N41900500)

Recent Advances in Catalytic Enantioselective Synthesis of α-Chiral Tertiary Azides^★

Yang Gao^a, Xuexin Zhang^a, Jinsheng Yu^a(), Jian Zhou^a^,^b^,^c()

a State Key Laboratory of Molecular & Process Engineering, Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
c Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou 571127

Received:2023-07-28 Published:2023-09-30
Contact: *E-mail: jsyu@chem.ecnu.edu.cn; jzhou@chem.ecnu.edu.cn
About author:
^★Dedicated to the 90th anniversary of Acta Chimica Sinica.
Supported by:
National Natural Science Foundation of China(21971067); National Natural Science Foundation of China(22171087); Innovation Program of Shanghai Municipal Education Commission(2023ZKZD37); Shanghai Science and Technology Innovation Action Plan(20JC1416900); Shanghai Science and Technology Innovation Action Plan(21N41900500)

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摘要/Abstract

α-手性叠氮化合物广泛应用于合成化学、药物化学和生命科学等领域. 由于手性叠氮既可用于多样性合成手性胺衍生物及含氮杂环化合物, 且叠氮基本身也是药效团, α-手性叠氮的高效合成对于药物研发十分重要. 随着引入手性季碳来增加分子的三维立体性来改善生物活性和成药性成为药物设计研发的有效手段, 发展具有氮杂季碳手性中心的α-手性三级叠氮的不对称催化合成新方法来促进药学研究十分必要. 然而, 由于叠氮基接近于直线的结构所带来的不利位阻效应, 以及需要区分差异性较小的取代基来构建氮杂季碳手性中心的挑战性, 高对映选择性的不对称催化方法较为匮乏. 本综述旨在从含C—N₃键化合物的不对称官能团化反应和通过C—N₃键形成的不对称叠氮化反应两种构建策略出发, 介绍近五年不对称催化合成α-手性三级叠氮的研究进展. 藉此对反应机理及优势与不足等进行分析讨论, 为从事有机合成和药物化学相关的科研人员提供一些参考和启发.

关键词: α-手性三级叠氮, 不对称催化合成, 叠氮化钠, 叠氮三甲基硅烷, 亲电叠氮化, 亲核加成

α-Chiral azides are widely used in the fields of synthetic chemistry, medicinal chemistry and life science. Owing to α-chiral azides can be used for the diverse synthesis of α-chiral amine derivatives and nitrogen-containing heterocycles, and its azido group is also a pharmacophore, the efficient synthesis of α-chiral azides is highly important for drug discovery and development. Along with the incorporation of chiral quaternary carbon that can increase the three-dimensional stereospecificity of molecules has become an effective strategy to improve the bioactivity and druggability in drug design and development, the development of catalytic asymmetric synthetic methods toward α-chiral tertiary azides featuring aza-quaternary carbon center is highly desirable to facilitate drug research. However, due to the adverse steric effects caused by the structure of azido group that is close to a straight line, and the challenge of distinguishing the substituents with less difference to construct the aza-quaternary carbon stereocenter, the catalytic asymmetric protocols with high enantioselectivity are relatively scarce. This review aims to summarize the advances of the past five years according to the following two strategies: asymmetric functionalizations of C—N₃ bond containing compounds and asymmetric azidations involving C—N₃ bond forming, as well as discusses the possible reaction mechanism, the advantages and disadvantages of different reactions, which would provide some references and inspiration for researchers engaged in organic synthesis and medicinal chemistry.

Key words: α-chiral tertiary azide, catalytic asymmetric synthesis, sodium azide, trimethylsilyl azide, electrophilic azidation, nucleophilic addition

引用此文

高杨, 张学鑫, 余金生, 周剑. α-手性三级叠氮化合物的不对称催化合成新进展^★[J]. 化学学报, 2023, 81(11): 1590-1608.

Yang Gao, Xuexin Zhang, Jinsheng Yu, Jian Zhou. Recent Advances in Catalytic Enantioselective Synthesis of α-Chiral Tertiary Azides^★[J]. Acta Chimica Sinica, 2023, 81(11): 1590-1608.

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图/表 24

图1. α-手性叠氮的代表性应用

Figure 1. The typical applications of α-chiral azides

图2. 不对称催化构建α-手性三级叠氮化合物的常见策略

Figure 2. Catalytic asymmetric strategies toward α-chiral tertiary azides

图3. 烯基叠氮与β,γ-不饱和-α-酮酸酯的不对称Diels-Alder反应

Figure 3. Asymmetric Diels-Alder reactions of vinyl azides with β,γ-unsaturated-α-ketoesters

图4. 烯基叠氮与醛亚胺的不对称[4+2]环加成及其串联反应

Figure 4. Asymmetric [4+2] cycloaddition and the related tandem reactions between vinyl azides and aldimines

图5. α-叠氮环状酮与醛亚胺的不对称Mannich反应

Figure 5. Asymmetric Mannich reaction of α-azido cyclic ketones with aldimines

图6. α-叠氮环状酮与靛红酮亚胺的不对称Mannich反应

Figure 6. Asymmetric Mannich reaction of α-azido cyclic ketones with isatin ketimines

图7. α-叠氮茚酮与硝基烯烃的不对称Michael加成反应

Figure 7. Michael addition of α-azido indanones to nitroolefins

图8. α-叠氮茚酮与β,γ-不饱和酮酸酯的不对称Michael加成反应

Figure 8. Asymmetric Michael addition of α-azido indanones to β,γ-unsaturated-α-ketoesters

图9. 砜基-PyBox配体实现α-三级叠氮的高选择性动力学拆分反应

Figure 9. Sulfonyl-PyBox enable kinetic resolution of α-tertiary azides

图10. α-手性三级叠氮酮和3-叠氮氧化吲哚的多样性转化

Figure 10. Diverse elaborations of chiral α-tertiary azidoketones and 3-azidooxindoles

图11. 手性铜催化β-萘酚的不对称去芳构化亲电叠氮化反应

Figure 11. Chiral Cu-catalyzed asymmetric dearomative electrophilic α-azidation of β-naphthols

图12. 铜催化不对称去芳构化叠氮化反应

Figure 12. Copper-catalyzed asymmetric dearomative azidation

图13. 手性铜催化3-三氟甲基氧化吲哚的不对称亲电叠氮化反应

Figure 13. Copper-catalyzed asymmetric electrophilic α-azidation of 3-trifluoromethylated oxindoles

图14. 手性锌络合物催化β-酮酸酯/酰胺的不对称亲电叠氮化反应

Figure 14. Zn-catalyzed asymmetric electrophilic α-azidation of β-ketoester/amides

图15. 辛可宁定催化的β-酮酸酯参与的不对称亲电叠氮化反应

Figure 15. Asymmetric α-azidation of β-ketoesters catalyzed by cinchonidine

图16. 外消旋2-溴-2-取代环状酮肟与NaN3的不对称叠氮化反应

Figure 16. Asymmetric azidation of α-bromo cyclic ketoximes with NaN3

图17. 外消旋α-溴-α-氰基酯与NaN3的不对称SN2X反应外消旋α-溴-α-氰基酯与NaN3的不对称SN2X反应

Figure 17. Asymmetric SN2X of α-bromo-α-cyanoesters with NaN3

图18. 外消旋α-溴-α-氰基酯与NaN3的不对称动力学拆分反应

Figure 18. Asymmetric kinetic resolution of α-bromo-α-cyanoesters with NaN3

图19. 酮酸酯的不对称氧化叠氮化反应

Figure 19. Asymmetric oxidative azidation of ketoesters

图20. 锰催化二氢吲哚的不对称C—H叠氮化反应

Figure 20. Enantioselective Mn-catalyzed C—H azidation of indolines

图21. 酶催化苯乙烯的不对称羟基叠氮化反应

Figure 21. Enzyme-catalyzed asymmetric hydroxyazidation of α-methyl styrene

图22. TMSN3实现的烯丙醇不对称卤叠氮化反应

Figure 22. Asymmetric haloazidation of allylic alcohols with TMSN3

图23. 阴离子铜络合物催化的丙烯酰胺的不对称自由基叠氮化反应

Figure 23. Anionic CN-box/Cu catalyzed asymmetric radical azidation of acrylamides

图24. 铁催化α-芳基烯酮的不对称自由基碳叠氮化反应

Figure 24. Fe-catalyzed asymmetric radical carboazidation of α-aryl enones

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α-手性三级叠氮化合物的不对称催化合成新进展^★

Recent Advances in Catalytic Enantioselective Synthesis of α-Chiral Tertiary Azides^★

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[2]	张春红, 张弘, 魏爱琳, 何旭敏, 夏海平. 由钌杂s-顺丁二烯化合物合成钌杂多环配合物的研究[J]. 化学学报, 2013, 71(10): 1373-1378.
[3]	袁华, 曹晨忠, 高硕. 拓扑量子方法及其在含C＝O和N＝O化合物性能估算中的应用[J]. 化学学报, 2010, 68(20): 2091-2098.
[4]	曹志娟, 刘彩云, 卢建忠. 化学发光新技术的研究——外参比校正法识别生物样品中的叠氮化钠[J]. 化学学报, 2004, 62(8): 794-798.

α-手性三级叠氮化合物的不对称催化合成新进展★

Recent Advances in Catalytic Enantioselective Synthesis of α-Chiral Tertiary Azides★

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α-手性三级叠氮化合物的不对称催化合成新进展^★

Recent Advances in Catalytic Enantioselective Synthesis of α-Chiral Tertiary Azides^★