Article
Chemistry, Organic
Chao Lin, Mao-Chang Wang, Peng Wie, Qi Xing, Chen-He Liu
Summary: A concise and efficient method for the synthesis of aziridines has been developed. The reaction proceeds through a [2+1] cycloaddition reaction of saccharin-derived cyclic ketimines with sulfur ylides. This methodology offers high atom-economy, broad substrate scope, and a simple procedure, resulting in excellent yields and diastereoselectivity (>20:1 dr). The aziridine products can be easily converted to benzothiazines through an unusual rearrangement reaction in the presence of base.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Sudip Baguli, Subham Sarkar, Soumajit Nath, Dibyendu Mallick, Debabrata Mukherjee
Summary: In this study, two thermally stable azomethine ylides were isolated, and it was found that they formed N-picoCAAC-CuCl complexes when reacted with CuCl. Computational analysis revealed that the pendant Npy and the softer nature of Cu(I) played crucial roles in this reaction. The resulting complexes can be used as highly active Rh(I) catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Kai-Xuan Yang, Dong-Sheng Ji, Haixue Zheng, Yucheng Gu, Peng-Fei Xu
Summary: This study investigates the inverse-electron-demand oxa-Diels-Alder reaction of 5-alkenyl thiazolones with beta,gamma-unsaturated carbonyl compounds enabled by quinine thiourea, allowing for the enantioselective synthesis of highly functionalized pyranthiazoles with three continuous stereocenters. This method is applicable to a wide range of substrates and has great potential for scalable synthesis and easy transformation.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Xing Gao, Dongyu Zhu, Feng Jiang, Jianning Liao, Wei Wang, Yongjun Wu, Lufei Zheng, Hongchao Guo
Summary: A diastereoselective (3 + 2) cycloaddition of N-sulfonyl ketimines with vinylethylene carbonates (VECs) has been developed, achieving good to excellent yields with moderate to good diastereoselectivities. An asymmetric version of this reaction was achieved using spiroketal-based diphosphine SKP as a chiral ligand, resulting in chiral products with >99% ee in most cases.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Mingyue Cui, Juan Li, Rongqiang Tian, Zheng Duan
Summary: A straightforward synthetic method was developed using tandem [5 + 1] carbonyl cyclization/[8 + 2] cycloaddition reactions of tropones and phosphiranes to synthesize structurally complex 6,5,7-fused tricyclic scaffolds. This one-pot reaction showed excellent regio- and periselectivity, with exclusive formation of the P-O bond and high-order [8 + 2] cycloaddition enabled by the highly reactive C=P bond.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Hong Hu, Bin-Shi Li, Jing-Lei Xu, Wei Sun, Yong Wang, Meng Sun
Summary: This study developed an unprecedented Rh(iii)-catalyzed reaction for the synthesis of spiro[4,5]dienone compounds. The method exhibits excellent selectivity and wide functional group tolerance.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Xing-Hai Fei, Yong-Long Zhao, Fen-Fen Yang, Xiang Guan, Zong-Qin Li, Da-Peng Wang, Meng Zhou, Yuan-Yong Yang, Bin He
Summary: A [4+3] annulation of 2-ylideneoxindoles with crotonate-derived sulfur ylides has been developed, leading to the synthesis of a series of oxepino[3,2-b]indoles in moderate to excellent yields. These synthetic oxepino[3,2-b]indoles can be further transformed into more complex cyclopropa[5,6]oxepino[3,2-b]indoles via a [2+1] cyclopropanation. Additionally, the synthetic compounds exhibit certain antiproliferative activity against K562 and MCF-7 cells, with IC50 values up to 5.40 +/- 0.88 μM and 18.41 +/- 0.50 μM, respectively.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Applied
I-Ting Chen, Ren-You Guan, Jeng-Liang Han
Summary: In this study, a catalytic asymmetric vinylogous Mannich/annulation/acylation reaction was developed for the synthesis of chiral spiro-oxindole piperidine derivatives with polyaromatic scaffolds. The reaction provided the desired products in good yields and high enantioselectivity. DFT computational calculations were used to explain the mechanism and origin of the observed enantioselectivity and O-acetylated products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Hongkai Sha, Yu Qian, Kuiyong Dong, Xinfang Xu, Wenhao Hu
Summary: A copper-catalyzed three-component reaction has been reported for the synthesis of acyclic thioacetal derivatives and medium-sized sulfur-containing heterocycles. The reaction proceeds by trapping highly active sulfur ylide species with isatin-derived ketimine, providing a broad substrate scope and good to high yields under mild reaction conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Physical
Santosh K. Pagire, Naoya Kumagai, Masakatsu Shibasaki
Summary: The catalytic asymmetric cyclopropanation of alpha,beta-unsaturated amides with stabilized sulfur ylides has been successfully achieved with high yields and selectivities, providing a new synthetic route for cyclopropanes.
Article
Chemistry, Physical
Peng-Yu Liang, Yang Dai, Ka Lu, Chao-Xian Yan, Yingzhe Liu, Pan-Pan Zhou, Zhaoyong Yang
Summary: The study successfully synthesized eight-membered cyclic ethers with important biological activities through the [4 + 4] domino annulation reaction catalyzed by DABCO. Quantum mechanical calculations revealed the reaction mechanism and the key steps were evaluated and explained using global and local reactivity indexes and the theory of intermolecular interactions.
COMPUTATIONAL AND THEORETICAL CHEMISTRY
(2021)
Review
Chemistry, Organic
Pavel Yu Ushakov, Sema L. Loffe, Alexey Yu Sukhorukov
Summary: This review summarizes the advancements made in [4 + 1]-annulation reactions involving sulfonium, sulfoxonium, and ammonium ylides, as well as diazo compounds and carbenes over the past six years. The newly emerged methods for generating A(4)-synthons, such as radical, transition metal-catalyzed, and photo-redox processes, are outlined. Specific focus is given to the progress in asymmetric [4 + 1]-annulations using organocatalysis and chiral ammonium ylides.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Yiming Zhou, Ning Li, Wei Cai, You Huang
Summary: A new sequential reaction has been developed for the synthesis of tetra-substituted 2,3-dihydrofurans with generally excellent yields and good diastereoselectivities. Chiral propargyl sulfonium salt can also be used for the synthesis of optically active 2,3-dihydrofurans with good enantioselectivities. The reaction sequence is designed based on the in situ generated 107r-conjugated structures from the dearomatization of indole fragments and subsequent intramolecular 1,6-addition.
Article
Chemistry, Organic
Mian Qi, Mengyao Li, Lu Bai, Jingjing Liu, Xinjun Luan
Summary: A novel [4 + 1] dearomative spiroannulation of alpha-halo-beta-naphthol and nitroolefin has been developed for the direct construction of various spiroisoxazolidines in high chemo-and diastereoselectivity. Notably, halophenols (X = Cl and I) were also tolerated by this reaction. Mechanistic studies revealed different routes for C(sp3)-X bond cleavage. The potential application of this method was exemplified by several further transformations.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Jie Huang, Shaofa Sun, Ping Ma, Jian Wang, Kevin Lee, Yalan Xing, Yang Wu, Gangqiang Wang
Summary: The highly diastereoselective spiro-cyclopropanation reaction developed in this study allows for efficient and selective synthesis of structurally interesting spiro-cyclopropanes under mild conditions. The method showcases excellent functional group compatibility and the potential for rapid transformation into complex indeno[1,2-c]pyridazine structures.
NEW JOURNAL OF CHEMISTRY
(2021)
