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★

doi:10.6023/A23040192

化学学报 ›› 2023, Vol. 81 ›› Issue (7): 793-808.DOI: 10.6023/A23040192 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

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)

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摘要/Abstract

邻羟基苯基取代的对亚甲基苯醌(p-QMs)是一类具有独特优势的p-QMs, 不仅保持了p-QMs原本的高反应活性, 随着羟基的引入, 此类合成砌块具有更加丰富的反应位点及手性调控位点, 极大地提高了此类合成砌块在合成化学、药物化学中的应用. 邻羟基苯基取代的p-QMs参与的催化不对称1,6-共轭加成反应、[4＋n]环加成反应近年来发展十分迅速, 为手性苯并含氧杂环、芳基甲烷等多种生物活性骨架的构建提供了高效的策略. 本文综述了邻羟基苯基取代的p-QMs参与的催化不对称反应, 指出了这一领域存在的挑战性问题, 将为设计邻羟基苯基取代的p-QMs参与的新型催化不对称反应提供新的思路.

关键词: 邻羟基苯基取代的对亚甲基苯醌, 不对称催化, 1,6-共轭加成, 环化反应

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

引用此文

杨爽, 王宁宜, 杭青青, 张宇辰, 石枫. 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^★[J]. 化学学报, 2023, 81(7): 793-808.

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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图/表 29

图1. 具有生物活性的手性含氧杂环及芳基甲烷衍生物

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

图2. 邻羟基苯基取代的p-QMs参与催化不对称反应的概况

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

图3. 邻羟基苯基取代的p-QMs与亚甲基靛红衍生物的催化不对称[4＋2]环加成反应

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

图4. 邻羟基苯基取代的p-QMs与腈类化合物的催化不对称[4＋2]环加成反应

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

图5. 邻羟基苯基取代的p-QMs与β-羰基醛的催化不对称[4＋2]环加成反应

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

图6. 邻羟基苯基取代的p-QMs与羟基马来酰亚胺的催化不对称[4＋2]环加成反应

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

图7. 邻羟基苯基取代的p-QMs与β-氧代酰基吡唑的催化不对称[4＋2]环加成反应

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

图8. 邻羟基苯基取代的p-QMs与吖内酯的催化不对称反电子需求的氧杂Diels-Alder反应

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

图9. 邻羟基苯基取代的p-QMs与吖内酯的催化不对称[4＋2]环加成反应

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

图10. 邻羟基苯基取代的p-QMs与吲哚烯的催化不对称[4＋2]环加成反应

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

图11. 邻羟基苯基取代p-QMs与烯胺的催化不对称[4＋2]环加成反应

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

图12. 邻羟基苯基取代p-QMs与炔胺的催化不对称[4＋2]环加成反应

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

图13. 邻羟基苯基取代的p-QMs与亚甲基噻唑酮的催化不对称[4＋2]环加成反应

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

图14. 邻羟基苯基取代的p-QMs与2,4-二烯醛的催化不对称[4＋2]环加成反应

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

图15. 邻羟基苯基取代的p-QMs与α-异腈乙酸乙酯的催化不对称[4＋2]环加成反应

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

图16. 邻羟基苯基取代的p-QMs与咪唑衍生α,β-不饱和酮的催化不对称[4＋2]环加成反应

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

图17. 邻羟基苯基取代的p-QMs与烯醛的催化不对称[4＋3]环加成反应

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

图18. 邻羟基苯基取代的p-QMs与乙烯基氮杂环丙烷的催化不对称[4＋3]环加成反应

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

图19. 邻羟基苯基取代的p-QMs与2-吲哚甲醇的催化不对称[4＋3]环加成反应

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

图20. 邻羟基苯基取代的p-QMs与2-吲哚甲醛的催化不对称[4＋3]环加成反应

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

图21. 邻羟基苯基取代的p-QMs与联烯酸酯的催化不对称[4＋1]环加成反应

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

图22. 邻羟基苯基取代的p-QMs与吡唑啉酮的催化不对称[4＋1]环加成反应

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

图23. 邻羟基苯基取代的p-QMs与α-卤代酮的催化不对称[4＋1]环加成反应

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

图24. 邻羟基苯基取代的p-QMs与重氮衍生物的催化不对称[4＋1]环加成反应

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

图25. 邻羟基苯基取代p-QMs与噻唑酮的催化不对称共轭加成反应

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

图26. 邻羟基苯基取代的p-QMs与芳基硼酸的催化不对称共轭加成反应

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

图27. 邻羟基苯基取代的p-QMs与芳香化合物的催化不对称傅-克烷基化反应

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

图28. 邻羟基苯基取代的p-QMs与α-硝基酮的催化不对称串联反应

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

图29. 邻羟基苯基取代的p-QMs与二级膦氧化物的催化不对称共轭加成反应

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^★

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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^★