Advances in Catalytic Asymmetric Reactions Involving o-Hydroxyphenyl Substituted p-Quinone Methides★

doi:10.6023/A23040192

Acta Chimica Sinica ›› 2023, Vol. 81 ›› Issue (7): 793-808.DOI: 10.6023/A23040192 Previous Articles Next Articles

Special Issue: 庆祝《化学学报》创刊90周年合辑

Review

邻羟基苯基取代的对亚甲基苯醌参与的催化不对称反应研究进展^★

杨爽^a, 王宁宜^a, 杭青青^a, 张宇辰^a^,^*(), 石枫^a^,^b^,^*()

a 江苏师范大学手性功能杂环研究中心化学与材料科学学院徐州 221116
b 常州大学石油化工学院常州 213164

投稿日期:2023-04-30 发布日期:2023-06-15

作者简介:

杨爽, 1999年出生于江苏宿迁, 2021年在徐州工程学院获得学士学位, 2021年至今在江苏师范大学化学与材料科学学院攻读硕士学位(导师: 石枫教授、张宇辰副教授). 研究领域是手性含氧杂环骨架的催化不对称构建.

王宁宜, 1998年出生于湖南宁远, 2020年在黑龙江科技大学获得学士学位, 2022年至今在江苏师范大学化学与材料科学学院攻读硕士学位(导师: 石枫教授、张宇辰副教授). 研究领域是轴手性杂环化合物的高对映选择性合成.

杭青青, 1995年出生于江苏泰州, 2018年在盐城师范学院获得学士学位, 2021年在江苏师范大学化学与材料科学学院获得硕士学位(导师: 石枫教授、张宇辰副教授). 研究领域是基于手性磷酸催化的不对称环加成反应构建手性杂环骨架.

张宇辰, 1989年出生, 江苏师范大学化学与材料科学学院副教授, 硕士生导师. 2019年毕业于中国科学技术大学有机化学专业, 获理学博士学位(导师: 龚流柱教授), 2019年入职江苏师范大学化学与材料科学学院. 主要从事手性生物活性分子的设计、催化不对称合成以及生物活性筛选等方面的研究工作.

石枫, 1976年出生, 理学博士, 江苏师范大学化学与材料科学学院教授, 常州大学石油化工学院特聘教授, 博士生导师, 国家杰出青年基金获得者. 2010年至2013年攻读了苏州大学与中国科学技术大学联合培养的博士学位, 2012年至2013年赴新加坡南洋理工大学从事访问学者工作. 主要从事催化不对称合成手性杂环的研究, 聚焦手性吲哚化学这一研究领域, 为构建结构复杂多样的手性杂环骨架提供了高效、高选择性的方法.

^★庆祝《化学学报》创刊90周年.

基金资助:
国家自然科学基金(22125104); 国家自然科学基金(21831007); 国家自然科学基金(22101103); 江苏省自然科学基金(BK20201018); 徐州市科技计划(KC21021)

Advances in Catalytic Asymmetric Reactions Involving o-Hydroxyphenyl Substituted p-Quinone Methides^★

Shuang Yang^a, Ningyi Wang^a, Qingqing Hang^a, Yuchen Zhang^a(), Feng Shi^a^,^b()

a Research Center of Chiral Functional Heterocycles, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116
b School of Petrochemical Engineering, Changzhou University, Changzhou 213164

Received:2023-04-30 Published:2023-06-15
Contact: *E-mail: zhangyc@jsnu.edu.cn; fshi@jsnu.edu.cn
About author:
^★Dedicated to the 90th anniversary of Acta Chimica Sinica.
Supported by:
National Natural Science Foundation of China(22125104); National Natural Science Foundation of China(21831007); National Natural Science Foundation of China(22101103); Natural Science Foundation of Jiangsu Province(BK20201018); Science and Technology Plan of Xuzhou City(KC21021)

o-Hydroxyphenyl substituted p-quinone methides (p-QMs) belong to a class of p-QMs with unique advantages. They not only maintain the high reactivity of p-QMs, but also have more reactive and activation sites owing to the introduction of hydroxyl group. Therefore, o-hydroxyphenyl substituted p-QMs have wide applications in synthetic and medicinal chemistry. The catalytic asymmetric 1,6-conjugate addition and [4＋n] cycloaddition of o-hydroxyphenyl substituted p-QMs have developed very rapidly in recent years, which have become efficient strategies for the synthesis of chiral oxygen-containing heterocycles and arylmethanes with potential bioactivity. This review summarizes the catalytic asymmetric reactions involving o-hydroxyphenyl substituted p-QMs and points out the remaining challenges in this research area, which will open a new window for the design of new type of o-hydroxyphenyl substituted p-QMs and their involved catalytic asymmetric reactions.

Key words: o-hydroxyphenyl substituted p-quinone methides, asymmetric catalysis, 1,6-conjugate addition, cycloaddition

Cite this article

Shuang Yang, Ningyi Wang, Qingqing Hang, Yuchen Zhang, Feng Shi. Advances in Catalytic Asymmetric Reactions Involving o-Hydroxyphenyl Substituted p-Quinone Methides^★[J]. Acta Chimica Sinica, 2023, 81(7): 793-808.

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Fig. & Tab. 29

Figure 1. Selected biologically active chiral oxygen-containing heterocycles and arylmethanes

Figure 2. Profile of catalytic asymmetric reactions of o-hydroxyphenyl substituted p-QMs

Figure 3. Catalytic asymmetric [4＋2] cycloaddition of o-hydroxyphenyl substituted p-QMs with methylene oxindoles

Figure 4. Catalytic asymmetric [4＋2] cycloaddition of o-hydroxyphenyl substituted p-QMs with nitrile derivatives

Figure 5. Catalytic asymmetric [4＋2] cycloaddition of o-hydroxyphenyl substituted p-QMs with β-carbonyl aldehydes

Figure 6. Catalytic asymmetric [4＋2] cycloaddition of o-hydroxyphenyl substituted p-QMs with hydroxymaleimides

Figure 7. Catalytic asymmetric [4＋2] cycloaddition of o-hydroxyphenyl substituted p-QMs with β-keto acylpyrazoles

Figure 8. Catalytic asymmetric inverse-electron-demand oxa-Diels-Alder reaction of o-hydroxyphenyl substituted p-QMs with azlactones

Figure 9. Catalytic asymmetric [4＋2] cycloaddition of o-hydroxyphenyl substituted p-QMs with azlactones

Figure 10. Catalytic asymmetric [4＋2] cycloadditions of o-hydroxyphenyl substituted p-QMs with vinylindoles

Figure 11. Catalytic asymmetric [4＋2] cycloaddition of o-hydroxyphenyl substituted p-QMs with enamides

Figure 12. Catalytic asymmetric [4＋2] cycloaddition of o-hydroxyphenyl substituted p-QMs with ynamides

Figure 13. Catalytic asymmetric [4＋2] cycloaddition of o-hydroxyphenyl substituted p-QMs with methylene thiazolones

Figure 14. Catalytic asymmetric [4＋2] cycloaddition of o-hydroxyphenyl substituted p-QMs with 2,4-dienals

Figure 15. Catalytic asymmetric [4＋2] cycloaddition of o-hydroxyphenyl substituted p-QMs with α‐isocyanoacetates

Figure 16. Catalytic asymmetric [4＋2] cycloaddition of o-hydroxyphenyl substituted p-QMs with imidazol-based α,β-unsaturated ketones

Figure 17. Catalytic asymmetric [4＋3] cycloadditions of o-hydroxyphenyl substituted p-QMs with enals

Figure 18. Catalytic asymmetric [4＋3] cycloaddition of o-hydroxyphenyl substituted p-QMs with vinyl aziridines

Figure 19. Catalytic asymmetric [4＋3] cycloaddition of o-hydroxyphenyl substituted p-QMs with 2-indolylmethanols

Figure 20. Catalytic asymmetric [4＋3] cycloaddition of o-hydroxyphenyl substituted p-QMs with 2-indolylaldehydes

Figure 21. Catalytic asymmetric [4＋1] cycloaddition of o-hydroxyphenyl substituted p-QMs with allenoates

Figure 22. Catalytic asymmetric [4＋1] cycloaddition of o-hydroxyphenyl substituted p-QMs with pyrazolones

Figure 23. Catalytic asymmetric [4＋1] cycloaddition of o-hydroxyphenyl substituted p-QMs with α?halogenated ketones

Figure 24. Catalytic asymmetric [4＋1] cycloaddition of o-hydroxyphenyl substituted p-QMs with diazo derivatives

Figure 25. Catalytic asymmetric conjugate addition of o-hydroxyphenyl substituted p-QMs with thiazolones

Figure 26. Catalytic asymmetric conjugate addition of o-hydroxyphenyl substituted p-QMs with arylboronic acid

Figure 27. Catalytic asymmetric Friedel-Crafts alkylation of o-hydroxyphenyl substituted p-QMs with aromatic compounds

Figure 28. Catalytic asymmetric cascade reaction of o-hydroxyphenyl substituted p-QMs with α-nitroketones

Figure 29. Catalytic asymmetric conjugate addition of o-hydroxyphenyl substituted p-QMs with secondary phosphine oxides

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邻羟基苯基取代的对亚甲基苯醌参与的催化不对称反应研究进展^★

Advances in Catalytic Asymmetric Reactions Involving o-Hydroxyphenyl Substituted p-Quinone Methides^★

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邻羟基苯基取代的对亚甲基苯醌参与的催化不对称反应研究进展★

Advances in Catalytic Asymmetric Reactions Involving o-Hydroxyphenyl Substituted p-Quinone Methides★

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Abstract

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Fig. & Tab. 29

References 60

Related Articles 15

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邻羟基苯基取代的对亚甲基苯醌参与的催化不对称反应研究进展^★

Advances in Catalytic Asymmetric Reactions Involving o-Hydroxyphenyl Substituted p-Quinone Methides^★