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2023 , Vol. 43 >Issue 3: 974 - 999

DOI: https://doi.org/10.6023/cjoc202211022

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 ,
  • 杨爽 ,
  • 张宇辰 ,
  • 石枫
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  • 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
† 共同第一作者.

收稿日期: 2022-11-16

  修回日期: 2023-01-17

  网络出版日期: 2023-02-07

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)

收起

Advances in Catalytic Asymmetric Reactions Involving o-Hydroxybenzyl Alcohols

  • Haiqing Wang ,
  • Shuang Yang ,
  • Yuchen Zhang ,
  • Feng Shi
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  • a School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116
    b School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164
† These authors contributed equally to this work.
* Corresponding authors. E-mail: ; ;

Received date: 2022-11-16

  Revised date: 2023-01-17

  Online published: 2023-02-07

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

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

本文引用格式

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 . DOI: 10.6023/cjoc202211022

Abstract

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

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