不对称构筑二芳基次甲基立体中心的研究进展

doi:10.6023/A21070345

化学学报 ›› 2021, Vol. 79 ›› Issue (11): 1303-1319.DOI: 10.6023/A21070345 上一篇下一篇

综述

不对称构筑二芳基次甲基立体中心的研究进展

尚阳, 肖检^*(), 王雅雯, 彭羽^*()

西南交通大学生命科学与工程学院四川省天然药物仿生合成工程研究中心成都 610031

投稿日期:2021-07-26 发布日期:2021-09-17
通讯作者: 肖检, 彭羽

作者简介:

尚阳, 1995年出生于四川南充, 2018年在重庆邮电大学获得学士学位. 2018年至2021年, 在彭羽教授指导下攻读并获得硕士学位. 研究兴趣是木脂素天然产物的全合成.

肖检, 1990年出生于四川巴中, 西南交通大学生命科学与工程学院助理研究员. 2018年在兰州大学功能有机分子化学国家重点实验室获得博士学位, 导师为彭羽教授. 2018年加入西南交通大学生命科学与工程学院化学系, 主要研究方向包括活性天然产物和药物分子的全合成、有机合成新方法发展等.

王雅雯, 西南交通大学生命科学与工程学院教授. 2000、2005年在兰州大学分别获得学士和博士学位, 导师为刘伟生教授. 曾任兰州大学化学化工学院教授. 主要研究领域为小分子荧光探针的合成及生物成像、超分子化学等.

彭羽, 西南交通大学生命科学与工程学院教授. 2000、2005年在兰州大学分别获得学士和博士学位, 导师为李卫东教授. 2008年至2009年在美国内华达大学里诺分校和加州大学圣芭芭拉分校做博士后研究, 合作导师为Liming Zhang教授. 曾任兰州大学化学化工学院和功能有机分子化学国家重点实验室教授. 主要研究领域为活性天然产物和药物分子的全合成、镍催化的还原环化新方法发展等.

基金资助:
国家自然科学基金(21772078); 国家自然科学基金(22071200); 四川省科技计划项目(2020JDRC0021); 中央高校基本科研业务费专项资金资助项目(2682020CX55); 中央高校基本科研业务费专项资金资助项目(2682021ZTPY011); 中央高校基本科研业务费专项资金资助项目(XJ2021KJZK004)

Advances on Asymmetric Construction of Diarylmethine Stereocenters

Yang Shang, Jian Xiao(), Yawen Wang, Yu Peng()

School of Life Science and Engineering, Sichuan Engineering Research Center for Biomimetic Synthesis of Natural Drugs, Southwest Jiaotong University, Chengdu 610031, China

Received:2021-07-26 Published:2021-09-17
Contact: Jian Xiao, Yu Peng
Supported by:
National Natural Science Foundation of China(21772078); National Natural Science Foundation of China(22071200); Science and Technology Department of Sichuan Province(2020JDRC0021); Fundamental Research Funds for the Central Universities(2682020CX55); Fundamental Research Funds for the Central Universities(2682021ZTPY011); Fundamental Research Funds for the Central Universities(XJ2021KJZK004)

文章分享

摘要/Abstract

二芳基次甲基结构单元广泛存在于具有重要生理和药理活性的天然产物和药物当中. 同时, 该结构单元中所特有的二芳基次甲基立体中心的对映选择性构筑往往也是天然产物全合成的难点和挑战性所在. 因此, 引起了众多有机合成化学家的研究兴趣. 近年来, 该手性立体中心的构建方法发展迅速, 新方法和新反应的报道也层出不穷; 开发出来的一些高效催化剂, 展示出独特的催化活性和选择性. 本文根据反应类型的不同, 将其分为不对称共轭加成反应和不对称氢化反应等六类, 综述近十年来二芳基次甲基立体中心的不对称构建方法及相关方法在天然产物全合成中的应用. 最后, 从全合成的角度进一步总结和分析未来构建二芳基次甲基手性立体中心的发展趋势, 力求发展更加高效、避免贵金属的催化剂及环境友好型的新方法和新试剂.

关键词: 二芳基次甲基, 不对称合成, 天然产物, 共轭加成, 偶联反应

Diarylmethine structure units are widely present in natural products and pharmaceuticals with important physiological and pharmacological activities. The enantioselective control of its stereogenic center, which is the most unique in this structure unit, has often become a difficulty and challenge during the research of total synthesis of natural products. Therefore, this field has attracted great interest to many organometallic chemists and synthetic organic chemists. In recent years, the construction methods of this stereocenter developed rapidly, and new reactions and reagents have emerged one after another. Some highly efficient catalysts have been invented, exhibiting unique catalytic activity and selectivity. In this review, according to the difference of reaction types, these methods can be divided into six types, such as asymmetric conjugate addition reaction (asymmetric 1,4-addition reactions involving aryl boronic acids, asymmetric 1,4-addition reactions involving aryl borates, enantioselective organocatalytic 1,4-addition reactions, asymmetric 1,4-conjugate addition induced by Evans chiral imide and asymmetric 1,6-conjugate addition of para-quinone methides), asymmetric allylation or propargylation of aromatic rings, transition metal-catalyzed asymmetric cross-coupling reaction, transition metal-catalyzed asymmetric C―H bond activation and functionalization, three-component reactions for asymmetric synthesis of 1,1-diaryl alkanes, asymmetric hydrogenation reactions for 1,1-diaryl alkanes, etc. This review aims to collect and summarize the asymmetric construction methods of diarylmethine stereogenic centers, and their applications in the total synthesis of natural products in the past decade. Finally, from the perspective of total synthesis, we further summarize and analyze the future development trend for the construction of diarylmethine chiral stereogenic centers, and encourage young generation to develop new methods and reagents that can avoid use of precious metals/catalysts and therefore are more efficient and environmentally friendly. More importantly, we hope that the developments of these practical methodologies can be further applied to asymmetric total synthesis of natural products and medicines, and eventually solve the source problem of these “useful molecules” with potential medicinal value.

Key words: diarylmethine, asymmetric synthesis, natural product, conjugate addition, coupling reaction

引用此文

尚阳, 肖检, 王雅雯, 彭羽. 不对称构筑二芳基次甲基立体中心的研究进展[J]. 化学学报, 2021, 79(11): 1303-1319.

Yang Shang, Jian Xiao, Yawen Wang, Yu Peng. Advances on Asymmetric Construction of Diarylmethine Stereocenters[J]. Acta Chimica Sinica, 2021, 79(11): 1303-1319.

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图/表 35

图1. 一些含有二芳基次甲基立体中心的天然产物和药物

Figure 1. Some natural products and medicines with diarylmethine stereogenic center

图2. 铑催化α,β-不饱和醛/酮与苯硼酸的1,4-共轭加成反应

Figure 2. Rh-catalyzed 1,4-conjugate addition of phenylboronic acids to α,β-unsaturated aldehydes/ketones

图3. 铑催化α,β-不饱和醛与芳基硼酸的不对称1,4-共轭加成反应

Figure 3. Rh-catalyzed asymmetric 1,4-conjugate addition of arylboronic acids to α,β-unsaturated aldehydes

图4. 铑催化γ,δ-不饱和β-酮酸酯与芳基硼酸的不对称1,4-共轭加成反应

Figure 4. Rh-catalyzed asymmetric 1,4-conjugate addition of arylboronic acids to γ,δ-unsaturated β-ketoesters

图5. 铑催化2-硝基苯乙烯与芳基硼酸的不对称1,4-共轭加成反应

Figure 5. Rh-catalyzed asymmetric 1,4-conjugate addition of arylboronic acids to 2-nitrostyrenes

图6. 以不对称1,4-共轭加成为关键反应的Montanine类型石蒜生物碱全合成

Figure 6. Total synthesis of montanine-type Amaryllidaceae alkaloids by asymmetric 1,4-conjugate addition

图7. 铑催化β,γ-不饱和α-酮酰胺与芳基硼酸的不对称1,4-共轭加成反应

Figure 7. Rh-catalyzed asymmetric 1,4-conjugate addition of arylboronic acids to β,γ-unsaturated α-ketoamides

图8. 铑催化α,β-不饱和亚胺酯与芳基硼酸的不对称1,4-共轭加成反应

Figure 8. Rh-catalyzed asymmetric 1,4-conjugate addition of arylboronic acids to α,β-unsaturated imino esters

图9. 铜催化α,β-不饱和酯与芳基硼酸的不对称1,4-共轭加成反应

Figure 9. Cu-catalyzed asymmetric 1,4-conjugate addition of arylboronic acids to α,β-unsaturated esters

图10. 有机催化α,β-不饱和醛/酮与芳基氟硼酸钾的不对称1,4-共轭加成反应

Figure 10. Organocatalyzed asymmetric 1,4-conjugate addition of aryl trifluoroborates to α,β-unsaturated aldehydes/ketones

图11. 铑催化α,β-不饱和酮/酯与芳氧甲基氟硼酸钾的不对称1,4-共轭加成反应

Figure 11. Rh-catalyzed asymmetric 1,4-conjugate addition of aryloxymethyl trifluoroborates to α,β-unsaturated ketones/esters

图12. 铜催化α,β-不饱和酮与芳基硼氧酯的不对称1,4-共轭加成反应

Figure 12. Cu-catalyzed asymmetric 1,4-conjugate addition of arylboroxines to α,β-unsaturated ketones

图13. 对映选择性有机催化的α,β-不饱和醛与富电子苯环的1,4-共轭加成反应

Figure 13. Enantioselective organocatalytic 1,4-conjugate addition of electron-rich benzenes to α,β-unsaturated aldehydes

图14. 有机小分子催化的不对称Friedel-Crafts烷基化/串联环化反应

Figure 14. Organocatalytic asymmetric Friedel-Crafts alkylation/cyclization cascade reaction

图15. 有机小分子催化芝麻酚与2-硝基苯乙烯的不对称Friedel-Crafts烷基化反应

Figure 15. Organocatalytic asymmetric Friedel-Crafts alkylation of sesamol with 2-nitrostyrenes

图16. 手性辅基诱导的不对称1,4-共轭加成反应在鬼臼毒素全合成中的应用

Figure 16. Application of asymmetric 1,4-conjugate addition reaction induced by chiral auxiliary in the total synthesis of podophyllotoxin

图17. 对亚甲基苯醌和其两性离子结构

Figure 17. para-Quinone methides and their zwitterionic structure

图18. 对亚甲基苯醌的催化不对称1,6-共轭加成反应

Figure 18. Asymmetric catalytic 1,6-conjugate addition of para-quinone methides

图19. 对亚甲基苯醌的催化不对称1,6-共轭加成反应: 邻二手性中心的构建

Figure 19. Asymmetric catalytic 1,6-conjugate addition of para-quinone methides to construct vicinal stereocenters

图20. 构建二芳基次甲基立体中心的催化不对称烯丙基取代反应

Figure 20. Catalytic asymmetric allylic substitution to construct diarylmethine stereocenter

图21. 构建二芳基次甲基立体中心的催化不对称炔丙基取代反应

Figure 21. Catalytic asymmetric propargylic substitution to construct diarylmethine stereocenter

图22. 镍催化的不对称交叉偶联反应

Figure 22. Ni-catalyzed asymmetric cross-coupling reaction

图23. 镍催化的不对称还原偶联反应

Figure 23. Ni-catalyzed asymmetric reductive cross-coupling reaction

图24. 钯催化的不对称交叉偶联反应

Figure 24. Pd-catalyzed asymmetric cross-coupling reaction

图25. 钯/镍催化芳基卤化物的分子内不对称还原Heck反应

Figure 25. Pd/Ni-catalyzed intramolecular asymmetric reductive Heck reaction of aryl halides

图26. 过渡金属催化的不对称C―H键芳基化反应

Figure 26. Transition-metal catalyzed asymmetric C―H arylation reaction

图27. 过渡金属催化的苄位不对称芳基化反应

Figure 27. Transition-metal catalyzed asymmetric benzylic arylation reaction

图28. 钯催化丙烯酸酯的不对称二芳基化反应

Figure 28. Pd-catalyzed asymmetric diarylation reaction of acrylates

图29. 利用芳基乙烯参与的三组分反应对映选择性构建二芳基次甲基立体中心

Figure 29. Enantioselective construction of diarylmethine stereocenter by three-component reaction with arylethylenes

图30. 二芳基乙烯及其衍生物的不对称氢化反应

Figure 30. Asymmetric hydrogenation of 1,1-diarylethene derivatives

图31. 二氢异喹啉衍生物的不对称氢化反应

Figure 31. Asymmetric hydrogenation of dihydroisoquinoline derivatives

图32. 铑催化重氮化合物与苯胺衍生物的不对称芳基化反应

Figure 32. Rh-catalyzed asymmetric arylation of diazo compounds with aniline derivatives

图33. 铑催化重氮化合物与苯胺衍生物的区域专一性和对映选择性芳基化反应

Figure 33. Rh-catalyzed regiospecific and enantioselective arylation of diazo compounds with aniline derivatives

图34. 手性磷酰胺配体参与的芳基硼酸与醛的催化不对称1,2-加成反应

Figure 34. Catalytic asymmetric 1,2-addition of arylboronic acids with aldehydes by chiral phosphoramide ligands

图35. 二芳基次甲基立体中心的不对称构建方法一览

Figure 35. Asymmetric construction of diarylmethine stereocenters

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不对称构筑二芳基次甲基立体中心的研究进展

Advances on Asymmetric Construction of Diarylmethine Stereocenters

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