Advances on Asymmetric Construction of Diarylmethine Stereocenters

doi:10.6023/A21070345

Acta Chimica Sinica ›› 2021, Vol. 79 ›› Issue (11): 1303-1319.DOI: 10.6023/A21070345 Previous Articles Next Articles

Review

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)

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

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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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Fig. & Tab. 35

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Figure 17. para-Quinone methides and their zwitterionic structure

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

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

Figure 20. Catalytic asymmetric allylic substitution to construct diarylmethine stereocenter

Figure 21. Catalytic asymmetric propargylic substitution to construct diarylmethine stereocenter

Figure 22. Ni-catalyzed asymmetric cross-coupling reaction

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

Figure 24. Pd-catalyzed asymmetric cross-coupling reaction

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

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

Figure 27. Transition-metal catalyzed asymmetric benzylic arylation reaction

Figure 28. Pd-catalyzed asymmetric diarylation reaction of acrylates

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

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

Figure 31. Asymmetric hydrogenation of dihydroisoquinoline derivatives

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

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

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

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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