Asymmetric synthesis of dihydrocoumarins via the organocatalytic hetero-Diels–Alder reaction of ortho-quinone methides

Lili Zhang, Yang Liu, Kun Liu, Zhantao Liu, Ningning He and Wenjun Li

Org. Biomol. Chem., 2017, 15, 8743
DOI: 10.1039/C7OB02325A

(4 + 2) cyclization of aza-o-quinone methides with azlactones: construction of biologically important dihydroquinolinone frameworks

Hai-Qing Wang, Wenjing Ma, Ao Sun, Xin-Yue Sun, Chao Jiang, Yu-Chen Zhang and Feng Shi

Org. Biomol. Chem., 2021, 19, 1334
DOI: 10.1039/D0OB02388D

Base-mediated diastereoselective [4 + 3] annulation of in situ generated ortho-quinone methides with C,N-cyclic azomethine imines

Jianfeng Xu, Shiru Yuan, Jingyi Peng, Maozhong Miao, Zhengkai Chen and Hongjun Ren

Org. Biomol. Chem., 2017, 15, 7513
DOI: 10.1039/C7OB01783A

Asymmetric synthesis of 3-aminodihydrocoumarins via the chiral guanidine catalyzed cascade reaction of azlactones

Sai Ruan, Xiaobin Lin, Lihua Xie, Lili Lin, Xiaoming Feng and Xiaohua Liu

Org. Chem. Front., 2018, 5, 32
DOI: 10.1039/C7QO00768J

Organocatalytic asymmetric addition of thioglycolates to o-quinone methides: a route to 5-substituted-5H-benzoxathiepine-2(3H)-ones

Chandan Gharui, Satya Prakash, Deepak Chopra and Subhas Chandra Pan

Org. Biomol. Chem., 2020, 18, 2828
DOI: 10.1039/D0OB00568A

Catalytic asymmetric 1,6-conjugate addition ofin situgeneratedpara-quinone methides with tritylthiol

Ya-Jing Fan, Lei Zhou and Shen Li

Org. Chem. Front., 2018, 5, 1820
DOI: 10.1039/C8QO00211H

3-Nitro-3,4-dihydrocoumarins: valuable precursors for the synthesis of enantiomerically enriched masked quaternary α-amino acid derivatives with a 3,4-dihydrocoumarin scaffold

Dan Lv, Min Zhao, Youming Wang and Zhenghong Zhou

Org. Biomol. Chem., 2019, 17, 9636
DOI: 10.1039/C9OB02089F

Diastereoselective synthesis of CF3-dihydrobenzofurans by [4+1] annulation of in situ-generated CF3-o-quinone methides and sulfur ylides

Babli K. Jha, Jaggaraju Prudhviraj, Prathama S. Mainkar, Nagender Punna and Srivari Chandrasekhar

RSC Adv., 2020, 10, 38588
DOI: 10.1039/D0RA08289A

Enantioselective one-pot synthesis of 4H-chromene derivatives catalyzed by a chiral Ni(ii) complex

Xuan Yu, Wenjie Lan, Jiaqi Li, Hui Bai, Zhaohai Qin and Bin Fu

RSC Adv., 2020, 10, 44437
DOI: 10.1039/D0RA08906K

Coumarin-3-formylpyrazoles as 3-carbon synthons in cyclocondensation for the synthesis of spiro-fused pentacyclic spirooxindoles

Chuan-Wen Lei, Chuan-Bao Zhang, Zhen-Hua Wang, Ke-Xin Xie, Jian-Qiang Zhao, Ming-Qiang Zhou, Xiao-Mei Zhang, Xiao-Ying Xu and Wei-Cheng Yuan

Org. Biomol. Chem., 2020, 18, 845
DOI: 10.1039/C9OB02434D

Recent advances in the application of Diels–Alder reactions involving o-quinodimethanes, aza-o-quinone methides and o-quinone methides in natural product total synthesis

Baochao Yang and Shuanhu Gao

Chem. Soc. Rev., 2018, 47, 7926
DOI: 10.1039/C8CS00274F

Phosphine-catalysed transformations of ortho- and para-quinone methides

Aitor Maestro and Mercedes Zurro

Org. Biomol. Chem., 2023, 21, 8244
DOI: 10.1039/D3OB01276J

Organocatalytic asymmetric [4+2] cyclization of 2-benzothiazolimines with azlactones: access to chiral benzothiazolopyrimidine derivatives

Qijian Ni, Xuyang Wang, Fangfang Xu, Xiaoyun Chen and Xiaoxiao Song

Chem. Commun., 2020, 56, 3155
DOI: 10.1039/D0CC00736F

Organocatalytic asymmetric [4 + 1] annulation of in situ generated ortho-quinomethanes with 4-halo pyrazolones: straightforward access to chiral spiro-benzofuran pyrazolones

Ming-Ming Chu, Suo-Suo Qi, Yi-Feng Wang, Biao Wang, Zhen-Hui Jiang, Dan-Qian Xu and Zhen-Yuan Xu

Org. Chem. Front., 2019, 6, 1977
DOI: 10.1039/C9QO00332K

Lewis acid-catalyzed tandem cyclization of in situ generated o-quinone methides and arylsulfonyl hydrazides for a one-pot entry to 3-sulfonylbenzofurans

Fan-Xiao Meng, Ruo-Nan Wang, Hong-Li Huang, Shu-Wen Gong, Qian-Li Li, Shao-Liang Zhang, Chun-Lin Ma, Chen-Zhong Li and Ji-Yuan Du

Org. Chem. Front., 2019, 6, 3929
DOI: 10.1039/C9QO01196J

Bifunctional Brønsted base catalyzed inverse-electron-demand aza-Diels–Alder reactions of saccharin-derived 1-azadienes with azlactones

Xiao-Rui Ren, Jun-Bing Lin, Xiu-Qin Hu and Peng-Fei Xu

Org. Chem. Front., 2019, 6, 2280
DOI: 10.1039/C9QO00357F

A Mn(iii)-catalysed domino process for C-3 substituted dihydrocoumarins from 2-hydroxybenzyl alcohols and 4-hydroxy-2H-chromen-2-ones

Gokul S. Londhe, Shankhajit Mondal and Boopathy Gnanaprakasam

Chem. Commun., 2025, 61, 11617
DOI: 10.1039/D5CC02950C

A visible light photoredox catalyzed carbon radical-mediated generation of ortho-quinone methides for 2,3-dihydrobenzofuran synthesis

Fan Zhou, Ying Cheng, Xiao-Peng Liu, Jia-Rong Chen and Wen-Jing Xiao

Chem. Commun., 2019, 55, 3117
DOI: 10.1039/C9CC00727J

An organic-base catalyzed asymmetric 1,4-addition of tritylthiol to in situ generated aza-o-quinone methides at the H2O/DCM interface

Xianghui Liu, Kai Wang, Wengang Guo, Yan Liu and Can Li

Chem. Commun., 2019, 55, 2668
DOI: 10.1039/C8CC09382B

Asymmetric organocatalytic conjugated addition of pyrazolin-5-ones to ortho-quinomethanes: construction of vicinal tertiary and all-carbon quaternary stereocenters

Ming-Ming Chu, Suo-Suo Qi, Wan-Zhen Ju, Yi-Feng Wang, Xue-Yang Chen, Dan-Qian Xu and Zhen-Yuan Xu

Org. Chem. Front., 2019, 6, 1140
DOI: 10.1039/C9QO00011A

Enantioselective synthesis of pyrano[2,3-c]pyrroleviaan organocatalytic [4 + 2] cyclization reaction of dioxopyrrolidines and azlactones

Yichen Wang, Yuzhen Chen, Xiaoping Li, Yukang Mao, Weiwen Chen, Ruoting Zhan and Huicai Huang

Org. Biomol. Chem., 2019, 17, 3945
DOI: 10.1039/C9OB00419J

Organocatalyzed Oxa-Diels–Alder Reactions: Recent Progress

Anup Biswas, Samrat Kundu, Dhananjoy Pal, Amit Pal and Modhu Sudan Maji

Synthesis, 2022, 54, 887
DOI: 10.1055/a-1514-1049

Squaramide Catalyzed Asymmetric Synthesis of Five‐ and Six‐Membered Rings

Anup Biswas, Avisek Ghosh, Rajat Shankhdhar and Indranil Chatterjee

Asian J Org Chem, 2021, 10, 1345
DOI: 10.1002/ajoc.202100181

Inverse‐Electron‐Demand Palladium‐Catalyzed Asymmetric [4+2] Cycloadditions Enabled by Chiral P,S‐Ligand and Hydrogen Bonding

Ya‐Ni Wang, Qin Xiong, Liang‐Qiu Lu, Qun‐Liang Zhang, Ying Wang, Yu Lan and Wen‐Jing Xiao

Angewandte Chemie, 2019, 131, 11129
DOI: 10.1002/ange.201905993

Organocatalytic Approach for Assembling Flavanones via a Cascade 1,4-Conjugate Addition/oxa-Michael Addition between Propargylamines with Water

Xinwei He, Mengqing Xie, Ruxue Li, Pui Ying Choy, Qiang Tang, Yongjia Shang and Fuk Yee Kwong

Org. Lett., 2020, 22, 4306
DOI: 10.1021/acs.orglett.0c01357

Catalytic Asymmetric Hydrophosphination of ortho-Quinone Methides

Xiu Gu, Hao Yuan, Jun Jiang, Yi Wu and Wen-Ju Bai

Org. Lett., 2018, 20, 7229
DOI: 10.1021/acs.orglett.8b03158

Catalytic Asymmetric [2+3] Cyclizations of Azlactones with Azonaphthalenes

Chun Ma, Jia‐Yu Zhou, Yi‐Zhu Zhang, Guang‐Jian Mei and Feng Shi

Angew Chem Int Ed, 2018, 57, 5398
DOI: 10.1002/anie.201801349

Enantioselective Synthesis of Functionalized 4-Aryl Hydrocoumarins and 4-Aryl Hydroquinolin-2-ones via Intramolecular Vinylogous Rauhut–Currier Reaction of para-Quinone Methides

Xiang-Zhi Zhang, Kang-Ji Gan, Xiao-Xue Liu, Yu-Hua Deng, Fang-Xin Wang, Ke-Yin Yu, Jing Zhang and Chun-An Fan

Org. Lett., 2017, 19, 3207
DOI: 10.1021/acs.orglett.7b01331

Asymmetric Aza-Diels–Alder Reactions of in Situ Generated β,β-Disubstituted α,β-Unsaturated N–H Ketimines Catalyzed by Chiral Phosphoric Acids

Shunlong He, Huanchao Gu, Yu-Peng He and Xiaoyu Yang

Org. Lett., 2020, 22, 5633
DOI: 10.1021/acs.orglett.0c01994

Formal intermolecular [4+1] cycloaddition reaction of in situ generated ortho-quinomethanes with CF3-Imidoyl sulfoxonium ylides and dual double bond isomerization cascade: Synthesis of trifluoromethyl-containing benzofuran derivatives

Youyan Wei, Chao Lin, Bo Li, Yixing Zhang and Shuzhou Xu

Tetrahedron, 2025, 173, 134454
DOI: 10.1016/j.tet.2025.134454

Organocatalytic Asymmetric Sequential 1,6-Addition/Acetalization of 1-Oxotetralin-2-carbaldehyde to ortho-Hydroxyphenyl-Substituted para-Quinone Methides for Synthesis of Spiro-3,4-dihydrocoumarins

Zhi-Pei Zhang, Li Chen, Xin Li and Jin-Pei Cheng

J. Org. Chem., 2018, 83, 2714
DOI: 10.1021/acs.joc.7b03177

Inverse‐Electron‐Demand Palladium‐Catalyzed Asymmetric [4+2] Cycloadditions Enabled by Chiral P,S‐Ligand and Hydrogen Bonding

Ya‐Ni Wang, Qin Xiong, Liang‐Qiu Lu, Qun‐Liang Zhang, Ying Wang, Yu Lan and Wen‐Jing Xiao

Angew Chem Int Ed, 2019, 58, 11013
DOI: 10.1002/anie.201905993

Lewis Acid Catalyzed Tandem 1,4-Conjugate Addition/Cyclization of in Situ Generated Alkynyl o-Quinone Methides and Electron-Rich Phenols: Synthesis of Dioxabicyclo[3.3.1]nonane Skeletons

Ji-Yuan Du, Yan-Hua Ma, Fan-Xiao Meng, Bao-Li Chen, Shao-Liang Zhang, Qian-Li Li, Shu-Wen Gong, Da-Qi Wang and Chun-Lin Ma

Org. Lett., 2018, 20, 4371
DOI: 10.1021/acs.orglett.8b01862

Catalytic Asymmetric [2+3] Cyclizations of Azlactones with Azonaphthalenes

Chun Ma, Jia‐Yu Zhou, Yi‐Zhu Zhang, Guang‐Jian Mei and Feng Shi

Angewandte Chemie, 2018, 130, 5496
DOI: 10.1002/ange.201801349

Phosphoric Acid Catalyzed Formation of Hydrogen-Bonded o-Quinone Methides. Enantioselective Cycloaddition with β-Dicarbonyl Compounds toward Benzannulated Oxygen Heterocycles

Fabian Göricke, Stefan Haseloff, Michael Laue, Maximilian Schneider, Thomas Brumme and Christoph Schneider

J. Org. Chem., 2020, 85, 11699
DOI: 10.1021/acs.joc.0c01375

Theoretical Investigation of the Enantioselective [4 + 2] Cycloaddition Reaction of o-Hydroxystyrene and Azlactone

Napassorn Jensupakarn, M. Paul Gleeson, Duangkamol Gleeson and Kanokthip Boonyarattanakalin

J. Org. Chem., 2019, 84, 4025
DOI: 10.1021/acs.joc.9b00032

Ni(ClO4)2‐Catalyzed Friedel–Crafts Reaction of Coumarin‐Fused Donor–Acceptor Cyclopropanes with Indoles: Stereoselective Synthesis of trans‐3,4‐Disubstituted‐3,4‐dihydrocoumarins

Jusung Lee, Kwang Min Ko and Sung‐Gon Kim

Eur J Org Chem, 2018, 2018, 4166
DOI: 10.1002/ejoc.201800669

Asymmetric Synthesis of Dihydrocoumarins via Squaramide‐Catalyzed [4 + 2] Annulation Reaction of 2‐Hydroxy α‐Amido Sulfones and Azlactones

Bin Pan, Fei‐Xiang He, Qiu‐Yu Liao, Ming Liu, Lei Zhu, Sheng‐Li Niu, Wu Liang, Fei Du, Ting Liu and Qin Ouyang

Chemistry An Asian Journal, 2025, 20
DOI: 10.1002/asia.70334

Straightforward Synthesis of Bifunctional Phosphorus Phenols via Phosphination of In Situ Generated o-Quinone Methides

Zhangpei Chen, Qinglong Shi, Gongshu Wang, Siwen Chen and Jianshe Hu

Molecules, 2018, 23, 1240
DOI: 10.3390/molecules23061240

Organocatalytic Enantioselective One‐pot Synthesis of Dihydrocoumarins via C−H Oxidation and Cyclization Cascade

Kyeong Seop Kim and Dae Young Kim

Asian J Org Chem, 2023, 12
DOI: 10.1002/ajoc.202300355

Organocatalytic stereoselective conjugate addition of 3-substituted oxindoles with in situ generated ortho-quinone methides

Weihong Liang, Wenhao Yin, Tingzhong Wang, Fayang G. Qiu and Junling Zhao

Tetrahedron Letters, 2018, 59, 1742
DOI: 10.1016/j.tetlet.2018.03.069

Selective synthesis of 2‐(5‐oxo‐1‐arylhex‐1‐yn‐3‐yl)phenyl benzoates via FeCl3‐mediated cascade reactions of propargylamines with β‐enamino ketones

Qiang Tang, Xinwei He, Jinxue Zhang, Tongtong Zhou, Mengqing Xie, Ruxue Li, Youpeng Zuo and Yongjia Shang

Applied Organom Chemis, 2020, 34
DOI: 10.1002/aoc.5676

Organocatalytic Asymmetric Tandem Cyclization/Michael Addition via Oxazol-5(2H)-One Formation: Access to Perfluoroalkyl-Containing N,O-Acetal Derivatives

Luyao Li, Tianxiao Yang, Tao Zhang, Bo Zhu and Junbiao Chang

J. Org. Chem., 2020, 85, 12294
DOI: 10.1021/acs.joc.0c01545

Asymmetric synthesis of pyrrolo[1,2-a]indoles via organocatalytic [3 + 2] annulation of substituted 2-vinylindoles with azlactones

Wulin Yang, Hao Wang, Zirong Pan, Zhong Li and Weiping Deng

Chinese Chemical Letters, 2020, 31, 721
DOI: 10.1016/j.cclet.2019.09.008

Construction of Quaternary Allylic Amino Acid Derivatives through Palladium-Catalyzed Allylic Alkylation Reaction of Azlactones with Vinyl Aziridine

Ke-Xin Huang, Zhao-Yang Chen, Xue-Guo Liu, Hong-Yong Ye and Wen-Chao Gao

Synthesis, 2022, 54, 4495
DOI: 10.1055/a-1878-8084

Electrochemically Induced Synthesis of Sulfonylated N-Unsubstituted Enamines from Vinyl Azides and Sulfonyl Hydrazides

Olga M. Mulina, Nataliya V. Zhironkina, Stanislav A. Paveliev, Dmitry V. Demchuk and Alexander O. Terent’ev

Org. Lett., 2020, 22, 1818
DOI: 10.1021/acs.orglett.0c00139

Divergent Asymmetric Reactions of ortho‐Quinone Methides with α‐Thiocyanato Indanones for the Synthesis of Spiro‐ and Fused‐Indanones

Xianghui Liu, Kai Wang, Yan Liu and Can Li

Chemistry A European J, 2021, 27, 735
DOI: 10.1002/chem.202003647

One-Pot Synthesis of 3,4-Dihydrocoumarins via C-H Oxidation/Conjugate Addition/Cyclization Cascade Reaction

Dae Young Kim

Molecules, 2023, 28, 6853
DOI: 10.3390/molecules28196853

Photoinduced reaction of potassium alkyltrifluoroborates, sulfur dioxide and para-quinone methides via radical 1,6-addition

Min Yang, Huiqi Han, Hui Jiang, Shengqing Ye, Xiaona Fan and Jie Wu

Chinese Chemical Letters, 2021, 32, 3535
DOI: 10.1016/j.cclet.2021.05.007

Synthesis of Trisubstituted 1,2,4‐Triazoles from Azlactones and Aryldiazonium Salts by a Cycloaddition/Decarboxylation Cascade

Xiao‐Ye Yu, Wen‐Jing Xiao and Jia‐Rong Chen

Eur J Org Chem, 2019, 2019, 6994
DOI: 10.1002/ejoc.201901467

Stereoselective synthesis of acyclic α,α-disubstituted α-amino acids derivatives from amino acids templates

Carlos Cativiela, Mario Ordóñez and José Luis Viveros-Ceballos

Tetrahedron, 2020, 76, 130875
DOI: 10.1016/j.tet.2019.130875

Dynamic Kinetic Resolution of Azlactones by Bifunctional Thioureas with α‑Trifluoromethyl or Methyl Groups

Eddy I. Jiménez, Margarita Cantú-Reyes, Miguel Flores-Ramos, Carlos A. Román-Chavarría, Howard Díaz-Salazar and Marcos Hernández-Rodríguez

Synlett, 2022, 33, 1751
DOI: 10.1055/a-1892-9911

Asymmetric Catalytic [4+5] Annulation of ortho‐Quinone Methides with Vinylethylene Carbonates and its Extension to Stereoselective Tandem Rearrangement

Xian‐Tao An, Ji‐Yuan Du, Zhi‐Long Jia, Qing Zhang, Ke‐Yin Yu, Yi‐Zhou Zhang, Xian‐He Zhao, Ran Fang and Chun‐An Fan

Chemistry A European J, 2020, 26, 3803
DOI: 10.1002/chem.201904903

Aromatizative Inverse‐Electron‐Demand Hetero‐Diels‐Alder Reaction in the Synthesis of Benzothiophene Derivatives

Maciej Saktura, Bartłomiej Joachim, Paulina Grzelak and Łukasz Albrecht

Eur J Org Chem, 2019, 2019, 6592
DOI: 10.1002/ejoc.201900884

Cycloaddition reactions of o-quinone methides with polarized olefins

Vitaly A. Osyanin, Anton V. Lukashenko and Dmitry V. Osipov

Russ. Chem. Rev., 2021, 90, 324
DOI: 10.1070/RCR4971

Cyclic 1‐Azadienes in the Organocatalytic Inverse‐Electron‐Demand Aza‐Diels‐Alder Cycloadditions

Anna Skrzyńska, Sebastian Frankowski and Łukasz Albrecht

Asian J Org Chem, 2020, 9, 1688
DOI: 10.1002/ajoc.202000332

Applications of Bifunctional Organocatalysts on ortho‐Quinone Methides

Soumendranath Mukhopadhyay, Chandan Gharui and Subhas Chandra Pan

Asian J Org Chem, 2019, 8, 1970
DOI: 10.1002/ajoc.201900466

Catalyst-Free 1,6-Conjugate Addition/Aromatization/Sulfonylation of para-Quinone Methides: Facile Access to Diarylmethyl Sulfones

Teng Liu, Jianjun Liu, Shubiao Xia, Jie Meng, Xianfu Shen, Xiufang Zhu, Wenchang Chen, Chengke Sun and Feixiang Cheng

ACS Omega, 2018, 3, 1409
DOI: 10.1021/acsomega.7b01745

Organocatalytic Stereoselective Synthesis of Dihydrocoumarins

Faisal Yasin Muhammad, Alemayehu Gashaw Woldegiorgis, Khadija Aimun, Suleman Muhammad and Zulfiqar Ali Khan

COC, 2025, 29, 599
DOI: 10.2174/0113852728331488240828074740

Synthesis of Chiral Pyrazolone and Spiropyrazolone Derivatives through Squaramide-Catalyzed Reaction of Pyrazolin-5-ones with o-Quinone Methides

Ji Zhou, Wen-Jun Huang and Guo-Fang Jiang

Org. Lett., 2018, 20, 1158
DOI: 10.1021/acs.orglett.8b00025

Formal (4 + 1)-Addition of Allenoates to o-Quinone Methides

Katharina Zielke and Mario Waser

Org. Lett., 2018, 20, 768
DOI: 10.1021/acs.orglett.7b03906

Conjugate Addition of 3‐Aryl Oxindoles to In Situ Generated o–Quinone Methides Without Essential Electronic or Steric Groups

Liu Song

Asian J Org Chem, 2024, 13
DOI: 10.1002/ajoc.202400370

Organocatalytic Asymmetric Domino Michael/Acyl Transfer Reaction Between α‐Nitroketones and in situ‐Generated ortho‐Quinone Methides: Route to 2‐(1‐Arylethyl)phenols

Chandan Gharui, Debasmita Behera and Subhas Chandra Pan

Adv Synth Catal, 2018, 360, 4502
DOI: 10.1002/adsc.201801015

Asymmetric Synthesis of Dihydrocoumarins through Chiral Phosphoric Acid-Catalyzed Cycloannulation of para-Quinone Methides and Azlactones

Zhi-Pei Zhang, Kai-Xue Xie, Chen Yang, Man Li and Xin Li

J. Org. Chem., 2018, 83, 364
DOI: 10.1021/acs.joc.7b02750

Recent Advances in Organocatalytic Asymmetric Cycloaddition Reactions Through Ortho‐Quinone Methide Scaffolds

Yu‐Hong Ma, Xiao‐Yu He, Qing‐Qing Yang, Amina Boucherif and Jun Xuan

Asian J Org Chem, 2021, 10, 1233
DOI: 10.1002/ajoc.202100141