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



王海清a, 杨爽a, 张宇辰a,*(), 石枫a,b,*()   

  1. 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 Wanga, Shuang Yanga, Yuchen Zhanga(), Feng Shia,b()   

  1. 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