邻羟基苄醇参与的催化不对称反应研究进展

doi:10.6023/cjoc202211022

有机化学 ›› 2023, Vol. 43 ›› Issue (3): 974-999.DOI: 10.6023/cjoc202211022 上一篇下一篇

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综述与进展

邻羟基苄醇参与的催化不对称反应研究进展

王海清^a, 杨爽^a, 张宇辰^a^,^*(), 石枫^a^,^b^,^*()

a 江苏师范大学化学与材料科学学院江苏徐州 221116
b 常州大学石油化工学院江苏常州 213164

收稿日期:2022-11-16 修回日期:2023-01-17 发布日期:2023-02-06
通讯作者: 张宇辰, 石枫
作者简介:
† 共同第一作者.
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-Hydroxybenzyl Alcohols

Haiqing Wang^a, Shuang Yang^a, Yuchen Zhang^a(), Feng Shi^a^,^b()

a School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116
b School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164

Received:2022-11-16 Revised:2023-01-17 Published:2023-02-06
Contact: Yuchen Zhang, Feng Shi
About author:
† These authors contributed equally to this work.
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); Technology Plan of Xuzhou City(KC21021)

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摘要/Abstract

邻亚甲基苯醌(o-QMs)是一类高反应活性的有机中间体, 在碳-碳键及碳-杂原子键的催化不对称构筑中发挥着重要作用. 但是, 该类中间体高度不稳定, 导致这类中间体参与的催化不对称反应发展缓慢. 利用前体原位产生o-QMs中间体可以有效解决这一问题. 因此, 发展原位产生的o-QMs中间体参与的催化不对称反应引起了化学工作者的关注. 而发展此类反应的关键是开发简便易得、结构稳定的o-QMs中间体前体. 邻羟基苄醇是一类具有独特优势的o-QMs前体, 近年来, 其参与的催化不对称[4+n]环加成反应、串联环化反应及亲核加成反应发展十分迅速, 已经成为合成手性含氧杂环及芳基甲烷衍生物的高效策略. 综述了邻羟基苄醇参与的催化不对称反应, 将为设计新型邻羟基苄醇及其参与的催化不对称反应提供新的思路.

关键词: 邻羟基苄醇, 邻亚甲基苯醌, 不对称催化, 环加成, 环化反应, 加成反应

Ortho-quinone methides (o-QMs) belong to a class of highly reactive organic intermediates, which play an important role in catalytic asymmetric formations of carbon-carbon bond and carbon-heteroatom bond. However, o-QMs are highly unstable, which led to the underdevelopment of catalytic asymmetric reactions involving o-QMs. The utilization of some precursors for in situ generating o-QMs is a solution to address this challenging issue. Therefore, the development of catalytic asymmetric reactions involving in situ generated o-QMs has absorbed great attention from the chemists. The key to develop such reactions is to exploit easily available and stable precursors of o-QMs. Ortho-hydroxybenzyl alcohols are a kind of o-QM precursors with unique advantages. Hence, the catalytic asymmetric [4+n] cycloadditions, tandem cyclizations and nucleophilic additions of o-hydroxybenzyl alcohols have developed very rapidly in recent years, which have become efficient strategies for the synthesis of chiral oxygen-containing heterocycles and arylmethane derivatives. The catalytic asymmetric reactions involving o-hydroxybenzyl alcohols are summarized, which will open a new window for the design of new type of o-hydroxybenzyl alcohols and their involved catalytic asymmetric reactions.

Key words: o-hydroxybenzyl alcohol, o-quinone methide, asymmetric catalysis, cycloaddition, cyclization, addition

引用此文

王海清, 杨爽, 张宇辰, 石枫. 邻羟基苄醇参与的催化不对称反应研究进展[J]. 有机化学, 2023, 43(3): 974-999.

Haiqing Wang, Shuang Yang, Yuchen Zhang, Feng Shi. Advances in Catalytic Asymmetric Reactions Involving o-Hydroxybenzyl Alcohols[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 974-999.

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图/表 36

图式1. o-QMs中间体前体的概述

Scheme 1. Profile of precursors of o-QMs intermediates

图式2. 邻羟基苄醇作为o-QMs前体的优势和反应特性

Scheme 2. Advantages and reactivities of o-hydroxybenzyl alcohols as the precursors of o-QMs

图式3. 邻羟基苄醇参与的催化不对称烯丙基取代反应

Scheme 3. Catalytic asymmetric allyl substitution reaction of o-hydroxybenzyl alcohols

图式4. 邻羟基苄醇与吲哚的催化不对称Friedel-Crafts烷基化反应

Scheme 4. Catalytic asymmetric Friedel-Crafts alkylation reaction of o-hydroxybenzyl alcohols with indoles

图式5. 邻羟基苄醇与1,3-二酮的催化不对称形式[4+2]环加成反应

Scheme 5. Catalytic asymmetric formal [4+2] cycloaddition reaction of o-hydroxybenzyl alcohols with 1,3-diketones

图式6. 邻羟基苄醇与1,3-环己二酮的催化不对称[4+2]环加成反应

Scheme 6. Catalytic asymmetric [4+2] cycloaddition of o-hydroxybenzyl alcohols with 1,3-cyclohexanediones

图式7. 邻羟基苄醇与α-重氮酯的催化不对称[4+2]环加成反应

Scheme 7. Catalytic asymmetric [4+2] cycloaddition of o-hydroxybenzyl alcohols with α-diazoesters

图式8. 邻羟基苄醇与吖内酯的催化不对称[4+2]环加成反应

Scheme 8. Catalytic asymmetric [4+2] cycloaddition of o-hydroxybenzyl alcohols with azlactones

图式9. 邻羟基苄醇与β-酮酸的催化不对称形式[4+2]环加成反应

Scheme 9. Catalytic asymmetric formal [4+2] cycloaddition of o-hydroxybenzyl alcohols with β-keto acids

图式10. 邻羟基苄醇与芳基取代乙醛的催化不对称[4+2]环加成反应

Scheme 10. Catalytic asymmetric [4+2] cycloaddition of o-hydroxybenzyl alcohols with aryl substituted acetaldehydes

图式11. 邻羟基苄醇与β-酮酯的催化不对称[4+2]环加成反应

Scheme 11. Catalytic asymmetric [4+2] cycloaddition of o-hydroxybenzyl alcohols with β-keto esters

图式12. 邻羟基苄醇与环状烯胺的催化不对称[4+2]环加成反应

Scheme 12. Catalytic asymmetric [4+2] cycloaddition between o-hydroxybenzyl alcohols with cyclic enamines

图式13. 邻羟基苄醇与3-甲基-2-烯基吲哚的催化不对称[4+2]环加成反应

Scheme 13. Catalytic asymmetric [4+2] cycloaddition of o-hydroxybenzyl alcohols with 3-methyl-2-vinylindoles

图式14. 邻羟基苄醇与苯乙烯的催化不对称[4+2]环加成反应

Scheme 14. Catalytic asymmetric [4+2] cycloaddition of o-hydroxybenzyl alcohols with styrenes

图式15. 邻羟基苄醇与芳基烯胺酮的区域选择性催化不对称[4+2]环加成反应

Scheme 15. Regioselective catalytic asymmetric [4+2] cycloaddition of o-hydroxybenzyl alcohols with aryl enaminones

图式16. 基于邻羟基苄醇与3-苯并呋喃甲醇的催化不对称[4+2]环加成反应合成Paeoveitol

Scheme 16. Synthesis of paeoveitol via catalytic asymmetric [4+2] cycloaddition of o-hydroxybenzyl alcohols with 3-benzofuryl methanols

图式17. 邻羟基苄醇与乙烯基硫醚的催化不对称[4+2]环加成反应

Scheme 17. Catalytic asymmetric [4+2] cycloaddition of o-hydroxybenzyl alcohols with vinyl thioethers

图式18. 邻羟基苄醇与芳基烯烃的催化不对称[4+2]环加成反应

Scheme 18. Catalytic asymmetric [4+2] cycloadditions of o-hydroxybenzyl alcohols with aryl alkenes

图式19. 邻羟基苄醇与2-炔丙基苯甲醇的催化不对称[4+2]环加成反应

Scheme 19. Catalytic asymmetric [4+2] cycloaddition of o-hydroxybenzyl alcohols with 2-propargyl benzyl alcohols

图式20. 乙烯基取代的邻羟基苄醇与炔醇或炔胺的催化不对称[4+2]环加成反应

Scheme 20. Catalytic asymmetric [4+2] cycloaddition of vinyl substituted o-hydroxybenzyl alcohols with alkynyl alcohols or alkynyl amines

图式21. 邻羟基苄醇与邻乙炔基苯乙酮的催化不对称[4+2]环加成反应

Scheme 21. Catalytic asymmetric [4+2] cycloaddition of o-hydroxybenzyl alcohols with o-alkynylacetophenones

图式22. 邻羟基苄醇与3-亚甲基异吲哚啉酮的催化不对称[4+2]环加成反应

Scheme 22. Catalytic asymmetric [4+2] cycloaddition of o-hydroxybenzyl alcohols with 3-methylene isoindolinones

图式23. 邻羟基苄醇与2-吲哚甲醇的催化不对称[4+3]环加成反应

Scheme 23. Catalytic asymmetric [4+3] cycloaddition of o-hydroxybenzyl alcohols with 2-indolylmethanols

图式24. 邻羟基苄醇与α-重氮酯的催化不对称[4+3]环加成反应

Scheme 24. Catalytic asymmetric [4+3] cycloaddition of o- hydroxybenzyl alcohols with α-diazoesters

图式25. 邻羟基苄醇与α-重氮酮的催化不对称重排[4+1]串联环化反应

Scheme 25. Catalytic asymmetric rearrangement [4+1] tandem cyclization of o-hydroxybenzyl alcohols with α-diazones

图式26. 邻羟基苄醇与α-重氮酯的催化不对称串联反应

Scheme 26. Catalytic asymmetric tandem reaction of o-hydroxybenzyl alcohols with α-diazoesters

图式27. 炔基邻羟基苄醇与α,β-不饱和醛的催化不对称串联环化反应

Scheme 27. Catalytic asymmetric tandem cyclization of alkynyl-substituted o-hydroxybenzyl alcohols with α,β-unsaturated aldehydes

图式28. 邻羟基苄醇与环丁酮甲酰胺的催化不对称串联环化反应

Scheme 28. Catalytic asymmetric tandem cyclization of o-hydroxybenzyl alcohols with cyclobutanone carboxamides

图式29. 邻羟基苄醇与1-乙炔基-2-萘酚的催化不对称串联环化反应

Scheme 29. Catalytic asymmetric tandem cyclization of o-hydroxybenzyl alcohols with 1-ethynyl-2-naphthols

图式30. 双取代的邻羟基苄醇与吲哚的催化不对称加成反应

Scheme 30. Catalytic asymmetric addition reaction of disubstituted o-hydroxybenzyl alcohols with indoles

图式31. 邻羟基苄醇与富电子芳烃的催化不对称加成反应

Scheme 31. Catalytic asymmetric addition reactions of o-hydroxybenzyl alcohols with electron-rich arenes

图式32. 手性路易斯酸催化下邻羟基苄醇与3-取代吲哚的不对称加成反应

Scheme 32. Asymmetric addition reaction of o-hydroxybenzyl alcohols with 3-substituted indole catalyzed by chiral Lewis acid

图式33. 邻羟基苄醇与3-萘基吲哚的催化不对称加成反应

Scheme 33. Catalytic asymmetric addition reaction of o-hydroxybenzyl alcohols with 3-naphthyl indoles

图式34. 邻羟基苄醇与呋喃的催化不对称加成反应

Scheme 34. Catalytic asymmetric addition reaction of o-hydroxybenzyl alcohols with furans

图式35. 邻羟基苄醇与杂原子亲核试剂的催化不对称加成反应

Scheme 35. Catalytic asymmetric addition reactions of o-hy- droxybenzyl alcohols with heteroatomic nucleophiles

图式36. 邻羟基苄醇与烯胺的催化不对称亲核加成反应

Scheme 36. Catalytic asymmetric addition reaction of o-hydroxybenzyl alcohols with enamines

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邻羟基苄醇参与的催化不对称反应研究进展

Advances in Catalytic Asymmetric Reactions Involving o-Hydroxybenzyl Alcohols

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