Recent advances in catalytic asymmetric reactions of Morita–Baylis–Hillman adducts

Xu-Hong Duan, Hui-Rui Du and Yong-Xing Song

Org. Chem. Front., 2025, 12, 2076
DOI: 10.1039/D4QO02212B

Design and organocatalytic synthesis of spirooxindole–cyclopentene–isoxazole hybrids as novel MDM2–p53 inhibitors

Xin Xie, Shan-Shan Xiong, Xiang Li, He Huang, Feng-Bo Wu, Peng-Fei Shen, Cheng Peng, Gu He and Bo Han

Org. Chem. Front., 2021, 8, 1836
DOI: 10.1039/D0QO01626H

Synthesis of spiro[2,3-dihydrofuran-3,3′-oxindole] derivatives via a multi-component cascade reaction of α-diazo esters, water, isatins and malononitrile/ethyl cyanoacetate

Taoda Shi, Shenghan Teng, Yajie Wei, Xin Guo and Wenhao Hu

Green Chem., 2019, 21, 4936
DOI: 10.1039/C9GC01751H

Phosphine-catalyzed asymmetric [4+1] annulation of activated α,β-unsaturated ketones with Morita–Baylis–Hillman carbonates: enantioselective synthesis of spirooxindoles containing two adjacent quaternary stereocenters

Fang-Le Hu, Yin Wei and Min Shi

Chem. Commun., 2014, 50, 8912
DOI: 10.1039/C4CC03479A

Enantioselective [3+2] annulation of isatin-derived MBH-carbonates and 3-nitroindoles enabled by a bifunctional DMAP-thiourea

Ming-Shun Mei, Yu-Hui Wang, Qing Hu, Qing-Hua Li, Da-Yu Shi, Dingding Gao, Guangbo Ge, Guo-Qiang Lin and Ping Tian

Chem. Commun., 2020, 56, 10718
DOI: 10.1039/D0CC04462H

α-Regioselective [3 + 2] annulations with Morita–Baylis–Hillman carbonates of isatins and 2-nitro-1,3-enynes

Guang-Yao Ran, Pan Wang, Wei Du and Ying-Chun Chen

Org. Chem. Front., 2016, 3, 861
DOI: 10.1039/C6QO00118A

Stereoselective synthesis and applications of spirocyclic oxindoles

Alexander J. Boddy and James A. Bull

Org. Chem. Front., 2021, 8, 1026
DOI: 10.1039/D0QO01085E

Recent advances in the annulation of Morita–Baylis–Hillman adducts

Neng-Jun Zhong, Yi-Zhan Wang, Liang Cheng, Dong Wang and Li Liu

Org. Biomol. Chem., 2018, 16, 5214
DOI: 10.1039/C8OB00929E

Reaction condition-dependent divergent synthesis of spirooxindoles and bisoxindoles

Guo-Shu Chen, Yu-Bo Fang, Zhi Ren, Xu Tian and Yun-Lin Liu

Org. Chem. Front., 2021, 8, 3820
DOI: 10.1039/D1QO00575H

Insights into Lewis base-catalyzed chemoselective [3 + 2] and [3 + 4] annulation reactions of MBH carbonates

Qianqian Deng, Shi-Jun Li, Donghui Wei and Yu Lan

Org. Chem. Front., 2020, 7, 1828
DOI: 10.1039/D0QO00457J

Organocatalytic asymmetric synthesis of multifunctionalized α-carboline-spirooxindole hybrids that suppressed proliferation in colorectal cancer cells

Xiang-Hong He, Xue-Ju Fu, Gu Zhan, Nan Zhang, Xiang Li, Hong-Ping Zhu, Cheng Peng, Gu He and Bo Han

Org. Chem. Front., 2022, 9, 1048
DOI: 10.1039/D1QO01785C

Catalyst-free Friedel–Crafts hydroxyalkylation of imidazo[1,2-α]pyridines with ethyl trifluoropyruvate

Ke Li, Xue-Mei Zhao, Fa-Liu Yang, Xiao-Han Hou, Yan Xu, Yan-Chun Guo, Xin-Qi Hao and Mao-Ping Song

RSC Adv., 2015, 5, 90478
DOI: 10.1039/C5RA15678E

Substrate-controlled switchable asymmetric annulations to access polyheterocyclic skeletons

Kai-Kai Wang, Pan Wang, Qin Ouyang, Wei Du and Ying-Chun Chen

Chem. Commun., 2016, 52, 11104
DOI: 10.1039/C6CC06148F

Asymmetric domino 1,6-addition/annulation reaction of 3-cyano-4-alkenyl-2H-chromen-2-ones with isatin-derived MBH carbonates: enantioselective synthesis of 3,3′-cyclopentenylspirooxindoles bearing 2H-chromen-2-ones

Zhen-Hua Wang, Chuan-Wen Lei, Xia-Yan Zhang, Yong You, Jian-Qiang Zhao and Wei-Cheng Yuan

Org. Chem. Front., 2019, 6, 3342
DOI: 10.1039/C9QO00890J

A highly efficient Mukaiyama–Mannich reaction of N-Boc isatin ketimines and other active cyclic ketimines using difluoroenol silyl ethers catalyzed by Ph3PAuOTf

Jin-Sheng Yu and Jian Zhou

Org. Biomol. Chem., 2015, 13, 10968
DOI: 10.1039/C5OB01895A

Diastereoselective synthesis of dispiro[indoline-3,3′-furan-2′,3′′-pyrrolidine] via [3 + 2]cycloaddition reaction of MBH maleimides of isatins and 1,3-dicarbonyl compounds

Liu-Na Pan, Jing Sun, Rong-Guo Shi and Chao-Guo Yan

Org. Chem. Front., 2020, 7, 3202
DOI: 10.1039/D0QO00845A

Morita–Baylis–Hillman adduct derivatives (MBHADs): versatile reactivity in Lewis base-promoted annulation

Peizhong Xie and You Huang

Org. Biomol. Chem., 2015, 13, 8578
DOI: 10.1039/C5OB00865D

New development in the enantioselective synthesis of spiro compounds

Aishun Ding, Marta Meazza, Hao Guo, Jung Woon Yang and Ramon Rios

Chem. Soc. Rev., 2018, 47, 5946
DOI: 10.1039/C6CS00825A

Access to highly enantioselective and diastereoselective spirooxindole dihydrofuran fused pyrazolones

Prakash K. Warghude, Abhijeet S. Sabale and Ramakrishna G. Bhat

Org. Biomol. Chem., 2020, 18, 1794
DOI: 10.1039/D0OB00007H

An expedient E-stereoselective synthesis of multi-substituted functionalized allylic boronates from Morita–Baylis–Hillman alcohols

Qingqing Xuan, Yahui Wei, Jinglong Chen and Qiuling Song

Org. Chem. Front., 2017, 4, 1220
DOI: 10.1039/C7QO00253J

Michael Addition Catalyzed by Chiral Secondary Amine Phosphoramide Using Fluorinated Silyl Enol Ethers: Formation of Quaternary Carbon Stereocenters

Jin‐Sheng Yu, Fu‐Min Liao, Wei‐Ming Gao, Kui Liao, Run‐Lin Zuo and Jian Zhou

Angewandte Chemie, 2015, 127, 7489
DOI: 10.1002/ange.201501747

The First Enantioselective Organocatalytic Synthesis of 3‐Spiro‐α‐Alkylidene‐γ‐Butyrolactone Oxindoles

Lucia Cerisoli, Marco Lombardo, Claudio Trombini and Arianna Quintavalla

Chemistry A European J, 2016, 22, 3865
DOI: 10.1002/chem.201504157

4‐(Dimethylamino)pyridine‐Catalyzed (3+2) Annulation of Pyrazoledione‐Derived Morita–Baylis–Hillman Carbonates with 2‐Arylideneindane‐1,3‐Diones: An Access to Dispirocyclic Compounds

Jianning Liao, Jiaqing Xu, Yongjun Wu, Yuxia Hou and Hongchao Guo

Adv Synth Catal, 2022, 364, 1074
DOI: 10.1002/adsc.202101251

Amine‐Catalyzed Tandem Reactions of Morita–Baylis–Hillman Acetates with Isatins: Facile Synthesis of 3‐Hydroxyoxindoles

Rongshun Chen, Xia Fan, Zhaozhong Xu and Zhengjie He

Eur J Org Chem, 2017, 2017, 6154
DOI: 10.1002/ejoc.201701274

Synthesis of Multifunctional α,α‐Difluoroketones through Allylic Alkylation of Difluoroenoxysilanes with MBH Carbonates

Bo‐Wen Pan, Yang Shi, You‐Ping Tian, Ying Zhou, Jian Zhou and Jin‐Sheng Yu

Chemistry An Asian Journal, 2020, 15, 4028
DOI: 10.1002/asia.202001145

Molecular Diversity of Base Promoted Annulation of MBH Carbonates of Isatins and Dialkyl But‐2‐ynedioates

Ting Tang, Xue‐Yan Liu, Jing Sun and Chao‐Guo Yan

ChemistrySelect, 2023, 8
DOI: 10.1002/slct.202302587

Stereoselective Access to Spirooxindoles and Bisoxindoles Through Organocatalyzed Asymmetric Divergent Transformations of Isatin‐derived MBH Carbonates

Yu‐Bo Fang, Xiao‐Tong Lin, Guo‐Shu Chen, Hai Ren, Dong‐Sheng Deng, Xiao‐Wei Hu, Yi‐Bing Xu, Shu‐Jie Chen and Yun‐Lin Liu

Chemistry An Asian Journal, 2021, 16, 3086
DOI: 10.1002/asia.202100792

Synthesis of dispirocyclohexadiene bisoxindole from Morita-Baylis-Hillman carbonate of isatin

Beom Kyu Min, Sangku Lee, Hwa Jung Roh, Ji Yeon Ryu, Junseong Lee and Jae Nyoung Kim

Tetrahedron Letters, 2017, 58, 3251
DOI: 10.1016/j.tetlet.2017.07.013

DABCO-catalyzed sp3 C–H activation: rapid access to isoxazole or coumarin-fused 3-quaternary carbon oxindoles and isoxazole-fused pyrrolidinones

Xiong-Li Liu, De-Hong Jing, Zhen Yao, Wen-Hui Zhang, Xiong-Wei Liu, Zhou-Jie Yang, Zhi Zhao, Ying Zhou and Xiao-Nian Li

Tetrahedron Letters, 2015, 56, 5637
DOI: 10.1016/j.tetlet.2015.08.059

Catalytic asymmetric synthesis of 3,3-disubstituted oxindoles: diazooxindole joins the field

Zhong-Yan Cao, Yu-Hui Wang, Xing-Ping Zeng and Jian Zhou

Tetrahedron Letters, 2014, 55, 2571
DOI: 10.1016/j.tetlet.2014.01.084

Sequential Assembly of Morita–Baylis–Hillman Carbonates and Activated ortho-Vinylbenzaldehydes To Construct Chiral Methanobenzo[7]annulenone Frameworks

Bo Jiang, Ben-Xian Xiao, Qin Ouyang, Hua-Ping Liang, Wei Du and Ying-Chun Chen

Org. Lett., 2019, 21, 3310
DOI: 10.1021/acs.orglett.9b01058

Highly Enantioselective [3 + 2]-Annulation of Isatin-Derived Morita–Baylis–Hillman Adducts with Cyclic Sulfonimines

Feng Wei, Hong-Yan Huang, Neng-Jun Zhong, Chun-Ling Gu, Dong Wang and Li Liu

Org. Lett., 2015, 17, 1688
DOI: 10.1021/acs.orglett.5b00456

Michael Addition Catalyzed by Chiral Secondary Amine Phosphoramide Using Fluorinated Silyl Enol Ethers: Formation of Quaternary Carbon Stereocenters

Jin‐Sheng Yu, Fu‐Min Liao, Wei‐Ming Gao, Kui Liao, Run‐Lin Zuo and Jian Zhou

Angew Chem Int Ed, 2015, 54, 7381
DOI: 10.1002/anie.201501747

Organocatalytic Asymmetric Allylic Alkylation of Morita–Baylis–Hillman Carbonates with Diethyl 2-Aminomalonate Assisted by In Situ Protection

Yu Zheng, Jing Wang, Peng-Ju Xia, Qing-lan Zhao, Jun-An Xiao, Hao-Yue Xiang, Xiao-Qing Chen and Hua Yang

J. Org. Chem., 2017, 82, 12202
DOI: 10.1021/acs.joc.7b02064

Organocatalyzed Dearomative Cycloaddition of 2-Nitrobenzofurans and Isatin-Derived Morita–Baylis–Hillman Carbonates: Highly Stereoselective Construction of Cyclopenta[b]benzofuran Scaffolds

Jian-Qiang Zhao, Lei Yang, Xiao-Jian Zhou, Yong You, Zhen-Hua Wang, Ming-Qiang Zhou, Xiao-Mei Zhang, Xiao-Ying Xu and Wei-Cheng Yuan

Org. Lett., 2019, 21, 660
DOI: 10.1021/acs.orglett.8b03786

Phosphine-Catalyzed Enantioselective [4 + 2] Cycloaddition–Semipinacol-Type-Rearrangement Reaction of Morita–Baylis–Hillman Carbonates

Yuan Zhong, Xiaoyun Zhao, Lu Gan, Sihua Hong and Xianxing Jiang

Org. Lett., 2018, 20, 4250
DOI: 10.1021/acs.orglett.8b01661

Organocatalytic Asymmetric Synthesis of α‐Trifluoromethyl Homoallylic Amine Derivatives from Trifluoromethyl‐Containing Ketoimines and Isatin‐Derived Morita‐Baylis‐Hillman Carbonates

Danna Chen, Yabo Deng, Shuo Sun, Pengfei Jia, Jinqi Huang and Wenjin Yan

Adv Synth Catal, 2023, 365, 178
DOI: 10.1002/adsc.202201091

Allylic Alkylation of Morita-Baylis-Hillman Carbonates with In Situ Generated Azomethine Ylides

Li-Wen Shen, Qin Zhao, Lu-Xin Zhou, Hui-Mei Liu, Yun-Qing Jia, Min Xiang and Guang-Wei Wang

LOC, 2025, 22, 395
DOI: 10.2174/0115701786348975241124171756

Lewis Base Promoted [4+2] Annulation of o‐Acylamino‐Aryl Morita‐Baylis‐Hillman Carbonates With Isatylidene Malononitriles: Facile Access to Spiro[Indolin‐3,2′‐Quinoline] Frameworks

Li‐Wen Shen, Mao‐Dan Luo, Wen‐Yi Zhou, Yuan‐Ying Luo, Min Xiang, Yun‐Qing Jia, Shu‐Pei Yuan and Guang‐Wei Wang

Journal of Heterocyclic Chem, 2024, 61, 2097
DOI: 10.1002/jhet.4919

One‐pot synthesis of spirooxindoles bearing α‐methylene‐γ‐butyrolactone moiety from Morita–Baylis–Hillman carbonates of isatins and paraformaldehyde

Junseong Lee and Jae Nyoung Kim

Bulletin Korean Chem Soc, 2024, 45, 1015
DOI: 10.1002/bkcs.12915

Theoretical investigation toward organophosphine‐catalyzed [3 + 3] annulation of Morita–Baylis–Hillman carbonates with azomethine imines: Mechanism, origin of stereoselectivity, and role of catalyst

Wei Zhang, Yan Qiao, Yang Wang, Mingsheng Tang and Donghui Wei

Int J of Quantum Chemistry, 2017, 117
DOI: 10.1002/qua.25367

Transformations of Modified Morita‐Baylis‐Hillman Adducts from Isatins Catalyzed by Lewis Bases

Zhi‐Chao Chen, Zhi Chen, Wei Du and Ying‐Chun Chen

The Chemical Record, 2020, 20, 541
DOI: 10.1002/tcr.201900058

Nucleophilic Difluoromethylenation of Ketones Using Diethyl (Difluoro(trimethylsilyl)methyl)phosphonate Mediated by 18-Crown-6 Ether/KOAc

Yu-Hui Wang, Zhong-Yan Cao and Jian Zhou

J. Org. Chem., 2016, 81, 7807
DOI: 10.1021/acs.joc.6b01457

Chemoselective Synthesis of Trifluoromethylated γ-Butenolide Derivatives via Phosphine-Promoted Tandem Reaction of Allylic Carbonates and Trifluoromethyl Ketones

Hua Xiao, Hong-yu Duan, Jun Ye, Ri-sheng Yao, Juan Ma, Zhe-zhe Yuan and Gang Zhao

Org. Lett., 2014, 16, 5462
DOI: 10.1021/ol502709w

Green oxidation of indoles using halide catalysis

Jun Xu, Lixin Liang, Haohao Zheng, Yonggui Robin Chi and Rongbiao Tong

Nat Commun, 2019, 10
DOI: 10.1038/s41467-019-12768-4

α-Regioselective Asymmetric [3 + 2] Annulations of Morita–Baylis–Hillman Carbonates with Cyclic 1-Azadienes and Mechanism Elucidation

Kai-Kai Wang, Tian Jin, Xin Huang, Qin Ouyang, Wei Du and Ying-Chun Chen

Org. Lett., 2016, 18, 872
DOI: 10.1021/acs.orglett.6b00189

Synthesis of spirooxindoles bearing 2,3-(or 2,5-)dihydrothiophene-2-thione moiety via [3+2] annulation of carbon disulfide with Morita-Baylis-Hillman carbonates of isatins

Beom Kyu Min, Gieun Kim, Hwa Jung Roh, Da Young Seo and Jae Nyoung Kim

Tetrahedron Letters, 2018, 59, 1674
DOI: 10.1016/j.tetlet.2018.03.056

ChemInform Abstract: Highly Diastereo‐ and Enantioselective [3 + 2] Annulation of Isatin‐Derived Morita—Baylis—Hillman Carbonates with Trifluoropyruvate Catalyzed by Tertiary Amines.

Neng‐Jun Zhong, Feng Wei, Qing‐Qing Xuan, Li Liu, Dong Wang and Yong‐Jun Chen

ChemInform, 2014, 45
DOI: 10.1002/chin.201413125

Enantioselective Synthesis of Spirooxindole‐Pyran and Furan Scaffolds via Copper‐Catalyzed Formal (3+3) and (3+2) Cycloaddition of Isatin‐Derived Propargylic Esters

Shweta Rohilla, Zahid Ahmad Khan and Vinod K. Singh

Chemistry A European J, 2025, 31
DOI: 10.1002/chem.202404005

Catalyst-free synthesis of 3-alkenyloxindoles from isatin-derived Morita–Baylis–Hillman carbonates

Lin Jiang, Yong-Gen Li, Hang Li, Ming-Wei Yuan, Yong-Ming Chuan, Hong-Li Li and Ming-Long Yuan

Journal of Chemical Research, 2017, 41, 160
DOI: 10.3184/174751917X14878812592652

Morita–Baylis–Hillman reaction of acrylamide with isatin derivatives

Radhey Mohan Singh, Kishor Chandra Bharadwaj and Dharmendra Kumar Tiwari

Beilstein J. Org. Chem., 2014, 10, 2975
DOI: 10.3762/bjoc.10.315

Organocatalytic Enantioselective [1 + 4] Annulation of Morita–Baylis–Hillman Carbonates with Electron-Deficient Olefins: Access to Chiral 2,3-Dihydrofuran Derivatives

Yuyu Cheng, Yuzhe Han and Pengfei Li

Org. Lett., 2017, 19, 4774
DOI: 10.1021/acs.orglett.7b02144

Convenient synthesis of chromene-fused spirocyclopentane-1,2-dioxindoles via base promoted annulation reaction

Kun Huang, Ting Tang, Ying Han, Jing Sun and Chao-Guo Yan

Tetrahedron Letters, 2025, 156, 155455
DOI: 10.1016/j.tetlet.2025.155455

Catalytic Asymmetric Synthesis of 3-Hydroxy-3-trifluoromethyl Benzofuranones via Tandem Friedel–Crafts/Lactonization Reaction

Hai Ren, Pan Wang, Lijia Wang and Yong Tang

Org. Lett., 2015, 17, 4886
DOI: 10.1021/acs.orglett.5b02440

Synthesis of Spirocyclic Oxindole Dihydrothiophenes by DBU-Catalyzed [3 + 2] Annulation of Morita–Baylis–Hillman Carbonates with Isothiocyanates

Yuan-Yuan Zhao, Shuai Zhao, Ji-Kang Xie, Xiu-Qin Hu and Peng-Fei Xu

J. Org. Chem., 2016, 81, 10532
DOI: 10.1021/acs.joc.6b01315

Chemoselective SN2′ Allylations of Detrifluoroacetylatively In Situ Generated 3-Fluoroindolin-2-one-Derived Tertiary Enolates with Morita–Baylis–Hillman Carbonates

Yi Zhu, Haibo Mei, Jianlin Han, Vadim A. Soloshonok, Jie Zhou and Yi Pan

J. Org. Chem., 2017, 82, 13663
DOI: 10.1021/acs.joc.7b02409

Organocatalytic Asymmetric Synthesis of Cyclic Compounds Bearing a Trifluoromethylated Stereogenic Center: Recent Developments

Xiang‐Hong He, Yan‐Ling Ji, Cheng Peng and Bo Han

Adv Synth Catal, 2019, 361, 1923
DOI: 10.1002/adsc.201801647

Highly diastereo- and enantioselective construction of phthalide-oxindole hybrids bearing vicinal quaternary chiral centers via an organocatalytic allylic alkylation

Wei Liu, Zhi-Peng Hu, Yan Yan and Wei-Wei Liao

Tetrahedron Letters, 2018, 59, 3132
DOI: 10.1016/j.tetlet.2018.07.002

Stereoselective and Regioselective Assembly of Spirooxindole [2,1‐b]furan Motifs through a Tandem Friedel–Crafts Alkylation/5‐exo‐dig‐Cyclization

Nandarapu Kumarswamyreddy and Venkitasamy Kesavan

Eur J Org Chem, 2016, 2016, 5301
DOI: 10.1002/ejoc.201601030

Insights into Organoamine-Catalyzed Asymmetric Synthesis of Axially Chiral Allenoates Using Morita–Baylis–Hillman Carbonates and Trisubstituted Allenoates: Mechanism and Origin of Stereoselectivity

Jiaming Zhang, Jing Luo, Xue Li, Qiaoyu Zhang, Zhoujie Wu, Yu Lan and Donghui Wei

J. Org. Chem., 2021, 86, 15276
DOI: 10.1021/acs.joc.1c01871

Silver(I) Oxide‐/DBU‐Promoted Synthesis of Dihydrofuran Units through Allenyl Silver Formation

Bao Yu, Anna Perfetto, Luca Allievi, Sabrina Dhambri, Marie‐Noelle Rager, Mohamed Selkti, Ilaria Ciofini, Marie‐Isabelle Lannou and Geoffroy Sorin

Chemistry A European J, 2020, 26, 17455
DOI: 10.1002/chem.202002696

Molecular diversity of the reactions of MBH carbonates of isatins and various nucleophiles

Zi-Ying Xiao, Jing Sun and Chao-Guo Yan

Beilstein J. Org. Chem., 2025, 21, 286
DOI: 10.3762/bjoc.21.21