不对称Petasis反应在手性胺类化合物合成中的应用

doi:10.6023/A21080391

化学学报 ›› 2021, Vol. 79 ›› Issue (11): 1345-1359.DOI: 10.6023/A21080391 上一篇下一篇

综述

不对称Petasis反应在手性胺类化合物合成中的应用

李翼^b, 徐明华^a^,^b^,^*()

a 南方科技大学化学系/深圳格拉布斯研究院广东省催化化学重点实验室深圳 518055
b 中国科学院上海药物研究所新药研究国家重点实验室上海 201203

投稿日期:2021-08-21 发布日期:2021-09-24
通讯作者: 徐明华

作者简介:

李翼, 2009年毕业于武汉大学, 获理学学士学位; 2014年毕业于中国科学院上海药物研究所, 获理学博士学位(导师: 徐明华研究员); 同年留所工作, 任助理研究员. 2016~2018年, 入选上海药明康德“青年人才计划”, 在国内新药研发部担任药物化学项目负责人, 主持创新药物研发项目, 全面负责小分子药物的临床前研究、开发及临床申报工作. 2018年至今, 在美国得克萨斯大学医学分部从事博士后研究. 主要研究兴趣包括不对称合成方法学, 以及针对肿瘤和糖尿病等重大疾病的创新药物研究.

徐明华, 南方科技大学化学系教授. 1999年博士毕业于中国科学院上海有机化学研究所, 先后在美国弗吉尼亚大学和乔治敦大学医学研究中心从事博士后研究; 曾任中国科学院上海药物研究所研究员、课题组长、博士生导师. 主要从事有机不对称合成及手性药物方面的研究, 致力于以一些重要有机分子及药物分子合成为导向的手性化学和手性技术探索, 发展高效不对称催化方法. 中国科学院“百人计划”、国家杰出青年科学基金获得者, 2016年获国家自然科学二等奖.

基金资助:
项目受国家自然科学基金(21971103); 广东省催化化学重点实验室(2020B121201002)

Applications of Asymmetric Petasis Reaction in the Synthesis of Chiral Amines

Yi Li^b, Ming-Hua Xu^a^,^b()

a Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, China
b State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China

Received:2021-08-21 Published:2021-09-24
Contact: Ming-Hua Xu
Supported by:
National Natural Science Foundation of China(21971103); Guangdong Provincial Key Laboratory of Catalysis(2020B121201002)

文章分享

摘要/Abstract

手性胺类化合物广泛存在于天然产物、药物分子和多功能材料中, 而且作为重要中间体、催化剂和手性辅剂在有机合成中也有广泛的应用, 因此, 发展高效的方法合成各种手性胺化合物及相应的骨架结构具有重要的科学意义和应用价值. 有机硼试剂、胺和羰基化合物参与的不对称Petasis三组分反应是构建手性胺及其衍生物最简洁、高效的方法之一. 近年来, 利用该策略来构建手性胺类化合物引起了广泛的关注. 文章综述了不对称Petasis反应合成手性胺类化合物的近期研究进展, 主要包括手性胺源、手性羰基化合物和手性硼试剂参与的底物诱导的不对称Petasis反应, 以及手性催化剂促进的不对称Petasis反应, 并对该领域的挑战和未来发展方向进行简要讨论.

关键词: Petasis反应, 手性胺, 硼酸, 不对称合成, 不对称催化

Chiral amines are valuable constituents of many natural products, pharmaceuticals and functional materials, they are also widely utilized as versatile building blocks and important chiral catalysts as well as chiral auxiliaries in organic synthesis. Therefore, it is of great scientific significance and application value to develop efficient methods for the synthesis of structurally diverse chiral amines and chiral amine scaffolds. In 1993, Petasis and co-workers reported an efficient synthesis of allylic amines through a Mannich-type reaction of vinylboronic acids with secondary amines and paraformaldehyde, where the organoboron reagents served as the nucleophilic component. Since then, this three-component Petasis reaction of organoboron reagents with amines and carbonyl derivatives has been developed as an appealing and concise method to access various amines. The asymmetric Petasis reaction provides a facile and efficient route to optically active amines and thus has attracted much attention over the past two decades. In this review, we summarize the recent progress achieved in the synthesis of chiral amines by asymmetric Petasis reaction and provide an overview on the methods applied for stereochemical control. The strategies that have been employed for accessing enantioenriched amines, including various chiral substrate-based diastereoselective induction approaches and several recent developments of enantioselective catalysis. In a large number of asymmetric Petasis reaction cases, good to high levels of stereoselectivities can be achieved relying on the utilization of chiral amine source, chiral carbonyl substrates, and chiral organoboron reagents. In particular, chiral amines such as α-methylbenzylamines and chiral α-hydroxy aldehyde analogues have emerged as a broadly applicable class of substrates for asymmetric Petasis reaction. The most promising advance has been the success of catalytic asymmetric Petasis reaction for enantioselective synthesis of chiral amines in the last few years. Chiral bifunctional thioureas and binaphthols have been demonstrated to be effective organocatalysts. Finally, the perspectives on the relevant challenges and future directions in this field are also discussed.

Key words: Petasis reaction, chiral amine, boronic acid, asymmetric synthesis, asymmetric catalysis

引用此文

李翼, 徐明华. 不对称Petasis反应在手性胺类化合物合成中的应用[J]. 化学学报, 2021, 79(11): 1345-1359.

Yi Li, Ming-Hua Xu. Applications of Asymmetric Petasis Reaction in the Synthesis of Chiral Amines[J]. Acta Chimica Sinica, 2021, 79(11): 1345-1359.

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图/表 51

图1. Petasis反应

Figure 1. Petasis reaction

图2. Petasis反应机理

Figure 2. Mechanism of Petasis reaction

图3. Petasis反应合成β,γ-烯基-α-氨基酸

Figure 3. Synthesis of β,γ-vinyl-α-amino acid by Petasis reaction

图4. 不对称Petasis反应合成β,γ-烯基-α-氨基酸

Figure 4. Synthesis of β,γ-vinyl-α-amino acid by asymmetric Petasis reaction

图5. Pd/C催化氢化脱除胺保护基

Figure 5. Removal of the amine protecting group by Pd-catalyzed hydrogenation

图6. 不对称Petasis反应合成α-芳基氨基酸衍生物

Figure 6. Synthesis of α-arylglycine derivative by asymmetric Petasis reaction

图7. 手性α-甲基苄胺介导的不对称Petasis反应

Figure 7. Chiral α-methylbenzylamine-induced asymmetric Petasis reaction

图8. 硼酸酯的不对称Petasis反应

Figure 8. Asymmetric Petasis reaction of boron ester

图9. (S)-苯甘氨醇介导的不对称Petasis反应

Figure 9. (S)-2-phenylglycinol-induced asymmetric Petasis reaction

图10. (S)-苯甘氨醇介导的不对称Petasis反应

Figure 10. (S)-2-Phenylglycinol-induced asymmetric Petasis reaction

图11. 3-吲哚硼酸的不对称Petasis反应

Figure 11. Asymmetric Petasis reaction of indole-3-boronic acid

图12. 手性炔丙基氨介导的不对称Petasis反应

Figure 12. Chiral propargylamine-induced asymmetric Petasis reaction

图13. 手性氨基磷酸酯介导的不对称Petasis反应

Figure 13. Chiral amino phosphonate-induced asymmetric Petasis reaction

图14. 不对称Petasis/RCM反应合成环状氨基酸酯

Figure 14. The synthesis of cyclic amino ester via asymmetric Petasis/ RCM reaction

图15. 烯丙基硼酸和靛红的不对称Petasis反应

Figure 15. Asymmetric Petasis reaction of allylboronic acid with isatin

图16. 烯丙基硼酸酯的不对称Petasis反应

Figure 16. Asymmetric Petasis reaction of allylboronic acid ester

图17. 异戊二烯基硼酸酯和联烯基硼酸酯的不对称Petasis反应

Figure 17. Asymmetric Petasis reaction of isoprenylboronates and allenylboronates

图18. 手性环己二胺介导的不对称Petasis反应

Figure 18. Chiral cyclohexane-1,2-diamine-induced asymmetric Petasis reaction

图19. 手性叔丁基亚磺酰胺介导的不对称Petasis反应

Figure 19. Chiral tert-butanesulfinamide-induced asymmetric Petasis reaction

图20. 手性β,γ-烯基-α-氨基酸衍生物的合成应用

Figure 20. Synthetic applicability of chiral β,γ-vinyl-α-amino acid derivatives

图21. InBr3介导的手性叔丁基亚磺酰胺的不对称Petasis反应

Figure 21. InBr3-induced asymmetric Petasis reaction of chiral tert-butanesulfinamide

图22. 手性β,γ-烯基-α-氨基酸衍生物的合成应用

Figure 22. Synthetic applicability of chiral β,γ-vinyl-α-amino acid derivatives

图23. 立体化学控制的机制

Figure 23. Mechanistic proposals for stereocontrol

图24. 杂芳基硼酸和手性叔丁基亚磺酰胺的不对称Petasis反应

Figure 24. Asymmetric Petasis reaction of heteroaryl boronic acid and chiral tert-butanesulfinamide

图25. 手性环状氨基醇的不对称Petasis反应

Figure 25. Asymmetric Petasis reaction of chiral cyclic amino alcohol

图26. 手性苏氨酸衍生物的不对称Petasis反应

Figure 26. Asymmetric Petasis reaction of chiral threonine derivatives

图27. 手性乳酸衍生物与伯胺的不对称Petasis反应

Figure 27. Asymmetric Petasis reaction of chiral lactic acid derivatives and primary amines

图28. 手性乳酸衍生物与仲胺的不对称Petasis反应

Figure 28. Asymmetric Petasis reaction of chiral lactic acid derivatives and secondary amines

图29. 三氟化硼介导的不对称Petasis反应

Figure 29. BF3-induced asymmetric Petasis reaction

图30. 手性α-羟基醛的不对称Petasis反应

Figure 30. Asymmetric Petasis reaction of chiral α-hydroxyl aldehyde

图31. 手性α-羟基醛和烯丙基氨的不对称Petasis反应

Figure 31. Asymmetric Petasis reaction of α-hydroxyl aldehyde and allylamine

图32. 手性乳香醇半缩醛的不对称Petasis反应

Figure 32. Asymmetric Petasis reaction of chiral lactol derivatives

图33. 手性糖类的不对称Petasis反应

Figure 33. Asymmetric Petasis reaction of chiral carbohydrate

图34. 手性乳酸衍生物和联烯硼酸酯的不对称Petasis反应

Figure 34. Asymmetric Petasis reaction of chiral lactic acid derivatives and allenylboronate

图35. 手性α-羟基醛衍生物和联烯硼酸酯的不对称Petasis反应

Figure 35. Asymmetric Petasis reaction of chiral α-hydroxyl aldehyde derivatives and allenylboronate

图36. 四组分不对称Petasis反应

Figure 36. Four components asymmetric Petasis reaction

图37. 手性α-氨基醛衍生物的不对称Petasis反应

Figure 37. Asymmetric Petasis reaction of chiral α-amino aldehyde derivatives

图38. 手性氮丙啶醛二聚体的不对称Petasis反应

Figure 38. Asymmetric Petasis reaction of chiral aziridine aldehyde dimers

图39. 手性α-氟代醛衍生物的不对称Petasis反应

Figure 39. Asymmetric Petasis reaction of chiral α-fluorine substituted aldehyde

图40. 手性(E)-苯乙烯基硼酸酯介导的不对称Petasis反应

Figure 40. Chiral (E)-styryl boron ester-induced asymmetric Petasis reaction

图41. 手性硼酯和手性α-甲基苄胺的不对称Petasis反应

Figure 41. Asymmetric Petasis reaction of chiral boron ester and chiral methylbenzylamine

图42. 手性硼酸介导的不对称Petasis反应

Figure 42. Chiral boronic acid-induced asymmetric Petasis reaction

图43. 手性硫脲催化的不对称Petasis反应

Figure 43. Chiral thiourea-catalyzed asymmetric Petasis reaction

图44. 手性硫脲催化的不对称Petasis反应

Figure 44. Chiral thiourea-catalyzed asymmetric Petasis reaction

图45. (S)-VAPOL催化的不对称Petasis反应

Figure 45. (S)-VAPOL-catalyzed asymmetric Petasis reaction

图46. (S)-VAPOL催化的不对称Petasis反应历程

Figure 46. The pathway of (S)-VAPOL-catalyzed asymmetric Petasis reaction

图47. 手性联萘酚催化的不对称Petasis反应

Figure 47. Chiral bipheol-catalyzed asymmetric Petasis reaction

图48. 手性联萘酚催化的不对称Petasis反应

Figure 48. Chiral bipheol-catalyzed asymmetric Petasis reaction

图49. 手性硫脲-联萘酚催化的不对称Petasis反应

Figure 49. Chiral thiourea-bipheol-catalyzed asymmetric Petasis reaction

图50. 手性联萘酚催化水杨醛的不对称Petasis反应

Figure 50. Chiral bipheol-catalyzed asymmetric Petasis reaction of salicylaldehyde

图51. 手性联萘酚催化水杨醛的不对称Petasis反应机理

Figure 51. Proposed mechanism of chiral bipheol-catalyzed asymmetric Petasis reaction of salicylaldehyde

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不对称Petasis反应在手性胺类化合物合成中的应用

Applications of Asymmetric Petasis Reaction in the Synthesis of Chiral Amines

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