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

doi:10.6023/A22040173

Acta Chimica Sinica ›› 2022, Vol. 80 ›› Issue (8): 1152-1164.DOI: 10.6023/A22040173 Previous Articles Next Articles

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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 发布日期:2022-09-01
通讯作者: 肖检, 彭羽

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(21772078); 国家自然科学基金(22071200); 四川省科技计划项目(2020JDRC0021); 中央高校基本科研业务费专项资金资助项目(2682021ZTPY011)

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

Lai Zhang, Jian Xiao(), Yawen Wang, Yu Peng()

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 Published:2022-09-01
Contact: Jian Xiao, Yu Peng
Supported by:
National Natural Science Foundation of China(21772078); National Natural Science Foundation of China(22071200); Science and Technology Department of Sichuan Province(2020JDRC0021); Fundamental Research Funds for the Central Universities(2682021ZTPY011)

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

Cite this article

Lai Zhang, Jian Xiao, Yawen Wang, Yu Peng. Recent Advances on the Construction of Chiral Dihydrobenzofurans by Asymmetric [3+2] Cyclization Reactions of Phenols (Quinones) and Alkenes[J]. Acta Chimica Sinica, 2022, 80(8): 1152-1164.

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Fig. & Tab. 22

Figure 1. Some natural products with chiral dihydrobenzofuran units

Figure 2. Synthetic methods of chiral dihydrobenzofuran units

Figure 3. Asymmetric [3+2] cyclization reactions induced by chiral auxiliary for the synthesis of (+)-dehydrodiconiferyl alcohol

Figure 4. Stereochemistry analysis of asymmetric [3+2] cyclization reactions induced by chiral auxiliary

Figure 5. Total synthesis of (+)-Adunctins C and D via asymmetric [3+2] cyclization reactions induced by chiral pool

Figure 6. Asymmetric [3+2] cyclization reactions catalyzed by chiral BINOL-derived phosphoric acid

Figure 7. Asymmetric synthesis of 2-amino-2,3-dihydrobenzofuran catalyzed by chiral BINOL-derived phosphoric acid

Figure 8. Asymmetric [3+2] cyclization reactions by biomimetic relay catalysis

Figure 9. Asymmetric [3+2] cyclization reactions catalyzed by spiro-chiral phosphoric acid

Figure 10. Asymmetric [3+2] cyclization reactions catalyzed by chiral diphenylprolinol trimethylsilyl ether

Figure 11. Asymmetric [3+2] cyclization reactions catalyzed by chiral diphenylprolinol silyl ether and enzyme or electrochemistry

Figure 12. Stereodivergent asymmetric [3+2] cyclization reactions catalyzed by chiral diarylprolinol trimethylsilyl ether

Figure 13. Asymmetric [3+2] cyclization reactions catalyzed by chiral oxazoline complex or spiropyrrolidine complex

Figure 14. Mechanism of asymmetric [3+2] cyclization reactions catalyzed by spiropyrrolidine complex

Figure 15. Pd-Catalyzed asymmetric [3+2] cyclization reactions of 2- bromophenols and 2,3-dihydrofurans

Figure 16. Pd-Catalyzed asymmetric [3+2] cyclization reactions of benzenediazonium tetrafluoroborates and alkenes

Figure 17. Mechanism of Pd-catalyzed asymmetric [3+2] cyclization reaction

Figure 18. Asymmetric [3+2] cyclization reactions catalyzed by chiral oxazaborolidinium ion

Figure 19. Asymmetric [3+2] cyclization reactions induced by chiral diol

Figure 20. Calalytic construction of chiral 2,3-disubstituted dihydrobenzofurans via C—H functionalization/oxa-Michael addition cascade

Figure 21. Construction of chiral bisdihydrobenzofuran structure via photo-irradiated asymmetric [3+2] cyclization reaction

Figure 22. Development of asymmetric [3+2] cyclization reactions for the construction of chiral dihydrobenzofurans

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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

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

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