Article
Chemistry, Organic
Jianning Liao, Jipan Dong, Jiaqing Xu, Wei Wang, Yongjun Wu, Yuxia Hou, Hongchao Guo
Summary: A phosphine-catalyzed [3 + 2] annulation reaction has been developed in this study to synthesize multifunctional isoxazoles with moderate to good yields and diastereoselectivities. The use of a spirocyclic chiral phosphine catalyst resulted in up to 89% ee.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yue Wang, Manman Song, Er-Qing Li, Zheng Duan
Summary: This study presents a new palladium/phosphine cooperative catalytic system for the synthesis of bicyclo[3.1.0]hexene derivatives, highlighting the crucial roles of both Pd and phosphine in the selective intermolecular activation of Morita-Baylis-Hillman carbonates. This strategy opens up a new avenue for efficient and economical metal/Lewis base dual catalytic systems and provides valuable clues on solving the limitations of selective activation.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Kai-Kai Wang, Jun Jing, Wen-Wen Zhou, Can Wang, Jun-Wei Ye, Ran Zhou, Ting-Ting Wang, Zhan-Yong Wang, Rongxiang Chen
Summary: A highly selective and divergent synthesis method for obtaining complex compounds was developed through Lewis base catalyzed switchable annulations of Morita-Baylis-Hillman carbonates with activated olefins. The reaction showed switchable [4 + 2] or [3 + 2] annulations via catalyst or substrate control, providing diverse architectures with high yields and excellent diastereoselectivities and regioselectivities. The synthetic utility of this strategy was further demonstrated through gram-scale experiments and simple transformations of the products.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ming-Shun Mei, Ya-Jie Wang, Gui-Shan Zhang, Jing-Yi Tang, Ping Tian, Yu-Hui Wang
Summary: The exploration of diastereodivergent synthesis of spirocyclic oxindoles has been challenging, but has been successfully achieved through asymmetric [3+2] annulations using two different chiral catalysts, resulting in two kinds of diastereomeric dispiro oxindoles with three contiguous stereogenic centers. The hexafluoroisopropanol (HFIP) additive plays a crucial role in accelerating the reaction and tuning diastereoselectivity. Moreover, the annulation adducts can be further converted to structurally diverse spirooxindoles.
Article
Chemistry, Organic
Xi Chen, Min Liu, Jiaqing Xu, Lei Wang, Songcheng Yu, Yongjun Wu, Jiaxing Huang, Hongchao Guo
Summary: A phosphine-catalyzed (3+2) annulation of Morita-Baylis-Hillman carbonates with pyrazolinone-derived ketimines has been achieved to give a variety of functionalized spirodihydropyrrole-dihydropyrazolones in moderate to high yields with good diastereoselectivities.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Congcong Geng, Xingfu Wei, Yongqiang Xu, Jianhui Liu, Lizeng Peng, Baomin Wang
Summary: A series of bisindole-annulated thiopyran frameworks were synthesized with good yields and diastereoselectivities through DMAP-catalyzed reactions, offering a novel synthetic strategy for valuable indole-annulated sulfur heterocycle derivatives, which may have potential applications in organic synthesis and medicinal chemistry.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Organic
Marta Papis, Raffaella Bucci, Alessandro Contini, Maria Luisa Gelmi, Leonardo Lo Presti, Giovanni Poli, Gianluigi Broggini, Camilla Loro
Summary: A phosphine-catalyzed domino assembly of six units of 2-bromomethyl acrylates was developed to synthesize polyalkenyl adducts containing two cyclohexenyl rings. This method involves initial dimerization and subsequent trimerization of the substrate, resulting in the formation of seven carbon-carbon bonds and four stereocenters. The protocol has also been successfully scaled up to gram-scale experiments.
Article
Chemistry, Organic
Meher Prakash, Rajni Lodhi, Sampak Samanta
Summary: An unprecedented substrate-controlled annulation method has been reported for the synthesis of angularly fused cyclopenta[c]chromenes and benzo[f]cyclopenta[d][1,2]-thiazepine 5,5-dioxide derivatives in good to high chemical yields. This method involves a Michael-initiated ring-expansion reaction that enables the formation of multiple bonds through a judicious choice of carbonucleophiles and cyclopropane scaffolds as carbon sources. The eco-friendly method is mild enough to protect various functionalities, and the prepared fused fulvene scaffolds can be smoothly transformed into a special class of hexahydrocyclopenta[c]chromenes in excellent yields.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Shutao Wang, Yongliang Gao, Shaoli Song, Xinze Li, Zhuoqi Zhang, Jinbao Xiang, Lianyou Zheng
Summary: This article describes a Lewis base catalyzed allylation reaction between N-aryl amides and various Morita-Baylis-Hillman (MBH) carbonates. The substrate scope of MBH carbonates and amides is comprehensively explored, making this approach useful for the synthesis of diversified branched tertiary N-allylic amides, with broad substrate scope, mild reaction conditions, and scalability.
Article
Chemistry, Organic
Jing Sun, Xueyan Liu, Qiu Sun, Ying Han, Chao-Guo Yan
Summary: Diverse functionalized dihydrobenzofuran spiro-indanedione scaffolds were synthesized via base-promoted cyclization reaction. The selective synthesis of two diastereomeric dispiro[indene-2,1′-cyclopenta[b]benzofuran-2,3′-indolines] was achieved using DABCO or DMAP as a base promoter. Moreover, DABCO or DMAP facilitated the annulation reaction of MBH formates, resulting in the formation of spiro[cyclopropa[c]chromene-1,2′-indene]-1′,3′-diones or dispiro[indene-2,1′-cyclopenta[b]benzofuran-2,3′-indolines]. Additionally, high-yielding and highly diastereoselective synthesis of dispiro[indene-2,5′-benzofuro[2′,3′:1,5]cyclopenta[1,2-c]pyrrole-4′,3″-indolines] was achieved using MBH maleimides.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Lei Zhang, Wangzhen Bao, Yuchen Liang, Wenjing Pan, Dongyang Li, Lichun Kong, Zhi-Xiang Wang, Bo Peng
Summary: This study demonstrates the reversal of stereoselectivity in MBH-type [3,3]-rearrangement by using a new pair of rearrangement partners, leading to the synthesis of different types of alpha-aryl alpha,beta-unsaturated carbonyl derivatives. Mechanistic studies provide insights into the reaction pathway and the opposite stereoselectivities observed.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Xing Guo, Boming Shen, Chang Liu, Hongyue Zhao, Xuechen Li, Peiyuan Yu, Pengfei Li
Summary: Based on the frontier molecular orbital theory, two types of modified enones have been designed and successfully applied in the chiral phosphine-catalyzed stereoselective [1 + 4]-annulation of MBH carbonates. The reaction proceeds smoothly under mild conditions, exhibiting excellent functional group tolerance and providing a broad scope of enantioenriched 2,3-dihydrofurans with high efficiency. DFT calculations have been used to guide the design of additional enones and understand the origin of stereoselectivity. Furthermore, this method explores the application scope of enones and enriches the chemistry of [1 + 4]-annulations of MBH carbonates for the preparation of optically active multifunctional 2,3-dihydrofurans.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Prashant Shukla, Ambika Asati, Devkumari Patel, Manorama Singh, Vijai K. K. Rai, Ankita Rai
Summary: This study reports on the Morita Baylis-Hillman (MBH) reaction using various aldehydes with acrylonitrile and methyl acrylate as electron-deficient alkenes. A novel catalyst, EDC.HCl, is utilized in the presence of CuI to synthesize the MBH adduct. The synthetic protocol shows excellent product yield (up to 99%), ambient reaction conditions, shorter reaction time, and no side product formation.
Article
Chemistry, Physical
Ricardo Lucas Gomes Pimentel, Rodolfo B. da Silva, Mario Luiz Araujo de Almeida Vasconcellos, Claudio Gabriel Lima-Junior, Fausthon F. da Silva
Summary: This study explores the synthesis and characterization of a mixed-metal copper-manganese iminodiacetate 1D coordination polymer (Cu/Mn-IDA) and its application as a catalyst for the Morita-Baylis-Hillman reaction. The results demonstrate that under optimized conditions, the catalyst can achieve yields of up to 87% for various aldehyde substrates. Additionally, the catalyst exhibits good recyclability.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Medicinal
Xiao-Jian Zhou, Jian-Qiang Zhao, Yue-Qin Lai, Yong You, Zhen-Hua Wang, Wei-Cheng Yuan
Summary: A readily available chiral cyclohexanediamine-derived bifunctional tertiary amine-squaramide catalyst has been developed for the asymmetric dearomative 1,3-dipolar cycloaddition reaction. The catalyst shows high efficiency, mild reaction conditions, excellent enantioselectivity, wide functional group tolerance, great potential for scale-up synthesis, and attractive product diversification.
Article
Chemistry, Organic
Pei-Hao Dou, Shu-Pei Yuan, Yan Chen, Jian-Qiang Zhao, Zhen-Hua Wang, Yong You, Yan-Ping Zhang, Ming-Qiang Zhou, Wei-Cheng Yuan
Summary: In this study, a palladium-catalyzed dearomatization process was developed using either 2-alkylidenetrimethylene carbonates or 2-(hydroxymethyl)-3-arylallyl carbonates to obtain a wide range of indoline-fused tetrahydropyrans in good yields with excellent diastereoselectivities. This reaction demonstrates the first application of pi-allyl palladium 1,4-[O,C]-dipole species in the dearomative cycloaddition of electron-deficient heteroarenes.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Li-Wen Shen, Yan-Ping Zhang, Yong You, Jian-Qiang Zhao, Zhen-Hua Wang, Wei-Cheng Yuan
Summary: A highly selective reaction method using inverse electron demand was developed, allowing the formation of diverse compounds in high yields. The reaction involved the interaction between unsaturated thioesters and 1,2,1,3-diazadienes, generated in situ from alpha-halo hydrazones.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Zhen-Hua Wang, Ji-Hong Liu, Yan-Ping Zhang, Jian-Qiang Zhao, Yong You, Ming-Qiang Zhou, Wen-Yong Han, Wei-Cheng Yuan
Summary: In this study, the enantioselective desymmetrization of N-arylmaleimides was achieved using a Cu(OTf)(2)/chiral ferrocenyl P,N-ligand complex as a catalyst, through the asymmetric 1,3-dipolar cycloaddition reaction of N-2,2,2-trifluoroethylisatin ketimines. A series of structurally diverse F3C-containing octahydropyrrolo[3,4-c]pyrroles, bearing four contiguous carbon stereocenters and one stereogenic chiral C-N axial bond, were obtained with excellent results (<= 99% yield, >20:1 dr, and 99% ee).
Article
Chemistry, Organic
Ting -Ting Li, Yong You, Ting-Jia Sun, Yan-Ping Zhang, Jian-Qiang Zhao, Zhen-Hua Wang, Wei-Cheng Yuan
Summary: A copper-catalyzed decarboxylative cascade cyclization of propargylic cyclic carbonates/carbamates with pyridinium 1,4-zwitterionic thiolates is developed, resulting in the efficient embedding of four new bonds (two C-C, one C-O/N, one C-S) and four new stereocenters into tetracyclic fused scaffolds in a single step, with moderate to good yields and excellent diastereoselectivities.
Article
Chemistry, Organic
Wei-Cheng Yuan, Lei Yang, Jian-Qiang Zhao, Hong-Yan Du, Zhen-Hua Wang, Yong You, Yan-Ping Zhang, Jiabin Liu, Wenjing Zhang, Ming-Qiang Zhou
Summary: A copper-catalyzed reaction of N-2,2,2-trifluoroethylisatin ketimines with benzo[b]thiophene sulfones was developed for the enantioselective 1,3-dipolar cycloaddition. The reaction afforded pentacyclic spirooxindoles containing pyrrolidine and benzo[b]sulfolane subunits in high efficiency and with excellent selectivity under mild conditions.
Article
Chemistry, Organic
Yong You, Ting-Ting Li, Ting-Jia Sun, Yan-Ping Zhang, Zhen-Hua Wang, Jian-Qiang Zhao, Wei-Cheng Yuan
Summary: A copper-catalyzed asymmetric decarboxylative propargylic substitution method was developed for the synthesis of compounds with vicinal quaternary-tetrasubstituted carbon stereo centers.
Article
Chemistry, Organic
Shun Zhou, Hui-Ling Qian, Jian-Qiang Zhao, Yong You, Zhen-Hua Wang, Jun-Qing Yin, Yan-Ping Zhang, Ming-Feng Chen, Wei-Cheng Yuan
Summary: A formal [4 + 2] cycloaddition reaction between 3-nitroindoles and ortho-aminophenyl p-quinone methides was developed through a dearomatization process. This method provides an efficient approach for the synthesis of tetrahydro-5H-indolo[2,3-b]quinolones with satisfactory results. The use of bifunctional Cinchona alkaloid-squaramide as the catalyst enabled the asymmetric version of the reaction, leading to the formation of chiral products with moderate to good enantioselectivities. This work represents the first dearomative cycloaddition of electron-deficient heteroarenes triggered by aza-Michael addition from p-QMs.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Zhen-Hua Wang, Tong Zhang, Li-Wen Shen, Xiu Yang, Yan-Ping Zhang, Yong You, Jian-Qiang Zhao, Wei-Cheng Yuan
Summary: Cycloaddition reactions between heteroaromatic N-ylides and electron-deficient olefins have been developed. The N-ylides, generated in situ from N-phenacylbenzothiazolium bromides, react smoothly with maleimides under mild conditions to yield fused polycyclic octahydropyrrolo[3,4-c]pyrroles in high yields. This reaction concept can also be extended to 3-trifluoroethylidene oxindoles and benzylidenemalononitriles, enabling the synthesis of highly functionalized polyheterocyclic compounds. A gram-scale experiment was carried out to demonstrate the practicality of the methodology.
Article
Biochemistry & Molecular Biology
Jun-Qing Yin, Yan-Ping Zhang, Yong You, Zhen-Hua Wang, Jian-Qiang Zhao, Qing Peng
Summary: In this study, DFT calculations were used to explore the properties of iron-silicon interface structures and found that the strong Fe-Si interaction affected the application of magnetic materials based on reconstructed Si surface.
Article
Biochemistry & Molecular Biology
Jian-Qiang Zhao, Wen-Jie Wang, Shun Zhou, Qi-Lin Xiao, Xi-Sha Xue, Yan-Ping Zhang, Yong You, Zhen-Hua Wang, Wei-Cheng Yuan
Summary: An unprecedented N-alkylation of 3-nitroindoles with para-quinone methides was developed for the first time. Using potassium carbonate as the base, a wide range of structurally diverse N-diarylmethylindole derivatives were obtained with moderated to good yields via the protection group migration/aza-1,6-Michael addition sequences. The reaction process was also demonstrated by control experiments.
Article
Biochemistry & Molecular Biology
Lin-Qiang Li, Jian-Qiang Zhao, Yan-Ping Zhang, Yong You, Zhen-Hua Wang, Zhen-Zhen Ge, Ming-Qiang Zhou, Wei-Cheng Yuan
Summary: In this research, a metal-free diastereoselective formal 1,3-dipolar cycloaddition reaction was developed for the desymmetrization of cyclopentene-1,3-diones using N-2,2,2-trifluoroethylisatin ketimines. The reaction efficiently leads to the formation of tetracyclic spirooxindoles containing pyrrolidine and cyclopentane subunits with good yields and diastereoselectivities. The methodology was also extended to trifluoromethyl-substituted iminomalonate, resulting in the formation of bicyclic heterocycles with fused pyrrolidine and cyclopentane moieties in moderate yields and high diastereoselectivities.
Article
Chemistry, Organic
Zhen-Hua Wang, Tong Zhang, Qing-Fei Yan, Jian-Qiang Zhao, Yong You, Yan-Ping Zhang, Jun-Qing Yin, Wei-Cheng Yuan
Summary: In this article, various α-aryl vinylsulfonium salts were successfully transformed under mild reaction conditions, leading to the synthesis of diverse 1,2-dihydroquinoline and ring-fused tetrahydroquinoline skeletons with moderate to excellent yields. The potential application of the method was demonstrated by scale-up experiments and further derivatizations of the products. The developed protocol offers mild and transition-metal-free reaction conditions, along with easy operation.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Review
Chemistry, Multidisciplinary
Yong You, Yan-Ping Zhang, Zhen-Hua Wang, Jian-Qiang Zhao, Jun-Qing Yin, Wei-Cheng Yuan
Summary: Copper-catalyzed decarboxylative reactions of propargylic cyclic carbonates/carbamates are an efficient way to construct various useful skeletons. The field has gained attention and made significant progress due to the reaction sites of propargylic cyclic carbonates/carbamates and the advantages of copper catalysis. This review addresses the achievements, mechanisms, synthetic applications, limitations, challenges, and opportunities in this field.
CHEMICAL COMMUNICATIONS
(2023)
Review
Chemistry, Organic
Zhen-Hua Wang, Yong You, Jian-Qiang Zhao, Yan-Ping Zhang, Jun-Qing Yin, Wei-Cheng Yuan
Summary: In conjugated pi systems, suitable strategies can generate pi-extended enolates from pronucleophiles and these tend to undergo stereoselective vinylogous reactions for remote functionalization. However, bench-stable unsaturated pronucleophiles have historically lacked proximal functionalization. Recent development of synthetic methods and catalytic systems have addressed this issue. This review highlights the achievements, mechanism insights, and challenges in the proximal functionalization of unsaturated pronucleophiles.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yong You, Guo-Ying Gan, Si-Yang Duan, Yan-Ping Zhang, Qun Li, Zhen-Hua Wang, Jian-Qiang Zhao, Xiong-Li Liu, Wei-Cheng Yuan
Summary: A highly enantioselective aza-Friedel-Crafts reaction was established for the synthesis of chiral tryptanthrin derivatives using chiral phosphoric acid as a catalyst. The synthesized compounds exhibited excellent yields and good to excellent enantioselectivities, and showed potential for medicinal applications, particularly in the treatment of leukemia.
ORGANIC CHEMISTRY FRONTIERS
(2023)