Advances in Catalytic Asymmetric Reactions Involving o-Hydroxybenzyl Alcohols

doi:10.6023/cjoc202211022

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (3): 974-999.DOI: 10.6023/cjoc202211022 Previous Articles Next Articles

Special Issue: 中国女科学家专辑

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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)

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

Cite this article

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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Fig. & Tab. 36

Scheme 1. Profile of precursors of o-QMs intermediates

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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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