苯酚(醌)与烯烃的不对称[3+2]环化反应: 手性二氢苯并呋喃的合成进展

doi:10.6023/A22040173

综述

苯酚(醌)与烯烃的不对称[3+2]环化反应: 手性二氢苯并呋喃的合成进展

张崃, 肖检^*, 王雅雯, 彭羽^*

四川省天然药物仿生合成工程研究中心西南交通大学生命科学与工程学院成都 610031

投稿日期:2022-04-14
通讯作者: *E-mail: xiaojian@swjtu.edu.cn; pengyu@swjtu.edu.cn
作者简介:张崃, 1995年出生于四川眉山, 2018年在西南科技大学获得学士学位. 2019年至2022年, 在彭羽教授指导下攻读并获得硕士学位. 研究兴趣是具有二氢苯并呋喃结构单元的黄烷酮类天然产物的全合成. 肖检, 1990年出生于四川巴中, 西南交通大学生命科学与工程学院助理研究员. 2018年在兰州大学功能有机分子化学国家重点实验室获得博士学位, 导师为彭羽教授. 2018年加入西南交通大学生命科学与工程学院化学系, 主要研究方向包括活性天然产物和药物分子的全合成、有机合成新方法发展等.王雅雯, 西南交通大学生命科学与工程学院教授. 2000、2005年在兰州大学分别获得学士和博士学位, 导师为刘伟生教授. 曾任兰州大学化学化工学院教授. 目前主要研究方向为小分子荧光探针的合成及生物成像、超分子化学等.彭羽, 西南交通大学生命科学与工程学院教授. 2000、2005年在兰州大学分别获得学士和博士学位, 导师为李卫东教授. 2008年至2009年在美国内华达大学里诺分校和加州大学圣芭芭拉分校做博士后研究, 合作导师为Liming Zhang教授. 曾任兰州大学化学化工学院和功能有机分子化学国家重点实验室教授. 目前主要研究方向为活性天然产物和药物分子的全合成、镍催化的还原环化新方法发展等
基金资助:
国家自然科学基金(Nos. 21772078 and 22071200), 四川省科技计划项目(No. 2020JDRC0021) 和中央高校基本科研业务费专项资金资助项目(No. 2682021ZTPY011).

Recent Advances on the Construction of Chiral Dihydrobenzofurans by Asymmetric [3+2] Cyclization Reactions of Phenols (Quinones) and Alkenes

Zhang Lai, Xiao Jian^*, Wang, Yawen, Peng Yu^*

Sichuan Engineering Research Center for Biomimetic Synthesis of Natural Drugs, School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031

Received:2022-04-14
Supported by:
National Natural Science Foundation of China (Nos. 21772078 and 22071200), the Science and Technology Department of Sichuan Province (No. 2020JDRC0021) and the Fundamental Research Funds for the Central Universities (No. 2682021ZTPY011).

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摘要/Abstract

二氢苯并呋喃结构单元广泛存在于具有良好生物活性和药用价值的天然产物之中, 因而引起了有机合成化学家和药物化学家们的关注. 针对该结构单元所包含的C2和C3邻二立体中心的对映选择性构建, 也是目前有机合成方法学研究的挑战性问题之一. 在众多解决方案中, 以苯酚(醌)与烯烃为底物, 具体采用催化不对称和手性辅剂诱导的[3+2]环化两种方式, 可以构建具有光学活性的二氢苯并呋喃结构单元. 本文将不同类型的手性催化剂和手性辅剂进行分类梳理, 综述了近年来不对称[3+2]环化反应的发展, 并重点剖析其中涉及的立体选择性控制. 同时, 简要介绍了该关键方法在二氢苯并呋喃天然产物合成中的应用. 为了启发更加高效和普适性的新催化体系出现, 最后总结和展望了不对称[3+2]环化反应的发展趋势.

关键词: 不对称[3+2]环化, 手性二氢苯并呋喃, 不对称催化, 手性辅剂, 邻二手性中心

Dihydrobenzofuran structural units are widely present in bioactive natural products, and therefore, this type of natural products have attracted extensive attention from synthetic organic chemists and pharmaceutical chemists. In recent years, enantioselective formation of this structural unit, especially its C2 and C3 vicinal chiral stereocenters, has always been one of challenging problems in the field of synthetic methodology. Among some methods, the construction of optically active dihydrobenzofuran structural units from [3+2] cyclizations of phenols (quinones) and olefins via asymmetric catalysis or induction by chiral auxiliaries developed rapidly. In this review, we summarized the recent progress of asymmetric [3+2] cyclization reactions with different types of chiral catalysts and auxiliaries, especially with emphasis on understanding the control of stereoselectivies in these methods. Meanwhile, the application in the total synthesis of dihydrobenzofurans enabled by asymmetric [3+2] cyclization reactions was briefly introduced. Finally, the future development trend of asymmetric [3+2] cyclization reactions was analyzed, in order to stimulate the emergence of highly efficient and general catalytic system.

Key words: asymmetric [3+2] cyclization, chiral dihydrobenzofuran, asymmetric catalysis, chiral auxiliary, vicinal stereocenters

引用此文

张崃, 肖检, 王雅雯, 彭羽. 苯酚(醌)与烯烃的不对称[3+2]环化反应: 手性二氢苯并呋喃的合成进展[J]. 化学学报, doi: 10.6023/A22040173.

Zhang Lai, Xiao Jian, Wang, Yawen, Peng Yu. Recent Advances on the Construction of Chiral Dihydrobenzofurans by Asymmetric [3+2] Cyclization Reactions of Phenols (Quinones) and Alkenes[J]. Acta Chimica Sinica, doi: 10.6023/A22040173.

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