Article
Chemistry, Physical
Yingqi Xia, Yingtang Ning, Minjie Liu, Fen -Er Chen
Summary: A poly(ethylene glycol) supported amino alcohol has been developed as a chiral ligand for the copper-catalyzed asymmetric nitrolaldol reaction. The catalyst enables the synthesis of syn-2-nitro-1,3-diols with high yields and stereoselectivities. The PEG moiety allows for easy purification and recycling of the catalyst.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Applied
Marcia R. R. Renio, Francisco J. P. M. Sousa, Nelia C. T. Tavares, Artur J. M. Valente, M. Elisa da Silva Serra, Dina Murtinho
Summary: The enantioselective Henry reaction is an important carbon-carbon bond forming reaction that requires the use of efficient chiral catalysts. In this study, in situ formed complexes of N-substituted dihydroxypyrrolidines were evaluated as catalysts, showing that the nature of the N-substituent significantly influences the outcome of the reaction. Best results were obtained using a Cu (II) complex of (3S,4S)-N-benzyl-3,4-dihydroxypyrrolidine, with products having er up to 92:8 (R:S).
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Liang Xu, Jia Cui, Shan Gao, Jianjun Wang, Jiao Liu, Hongge Jia, Zhuanfang Zhang, Fengjuan Miao, Yu Zang
Summary: Chiral conjugated microporous polymers (CCMPs) containing amide groups were designed and synthesized for the first time as heterogeneous asymmetric catalyst platforms for the stabilization of Pd in asymmetric catalytic synthesis. Four Pd/CCMPs heterogeneous catalysts exhibited efficient catalytic activity and excellent enantioselectivity in the asymmetric Henry reaction, with a wide range of substrates and easy recovery. The Pd/CCMPs composites could be easily recycled and maintained catalytic activity after 3 cycles of reactions.
MICROPOROUS AND MESOPOROUS MATERIALS
(2022)
Article
Chemistry, Multidisciplinary
Masahiro Kawada, Ryo Tsuyusaki, Kosuke Nakashima, Misaki Yamada, Akihiro Kozakai, Yasuyuki Matsushima, Shin-ichi Hirashima, Tsuyoshi Miura
Summary: This study presents the first successful example of asymmetric 1,2-additions of nitromethane to trifluoromethyl enones, and achieved highly functionalized products with high yields and excellent enantioselectivities through a novel N,N-dibenzyl diaminomethylenemalononitrile organocatalyst.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Wei Zhao, Wenji Wang, Huan Zhou, Qishan Liu, Zhiqing Ma, Haizhou Huang, Mingxin Chang
Summary: A one-pot asymmetric hydrogenation of pyridines with subsequent N-alkylation using a traceless Bronsted acid activation strategy is reported. The reaction exhibits high stereoselectivity and can be used to synthesize indolizidines and quinolizidines. Experimental and theoretical studies reveal that chloride anion and noncovalent interactions play important roles in determining the stereoselectivity of the reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Lin Liu, Kai-Xin Guo, Yu Tian, Chang-Jiang Yang, Qiang-Shuai Gu, Zhong-Liang Li, Liu Ye, Xin-Yuan Liu
Summary: The copper-catalyzed asymmetric cross-coupling of C(sp(3))-C(sp) bonds with terminal alkynes reported in this study shows high to excellent enantioselectivity. The rational design of chiral oxazoline-derived ligands is critical for success in tolerating oxidative conditions and inducing challenging enantiocontrol. This approach offers direct access to a variety of synthetically useful compounds and has great potential for the synthesis of enantioenriched medicinally relevant compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Ming Cui, Zhi-Yuan Zhao, Martin Oestreich
Summary: Chiral bis(phosphine) monooxides derived from C-2-symmetric bis(phosphines) have been found to exhibit superior enantioselection in copper-catalyzed conjugate borylation and 1,6-addition reactions. Specifically, (R,R)-Bozphos ligand shows significantly higher enantiomeric excesses and chemical yields compared to parent (R,R)-Me-Duphos ligand.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Bastian Jakob, Andreas M. Diehl, Kathrin Horst, Harald Kelm, Georg Manolikakes
Summary: Here we report a palladium-catalyzed asymmetric three-component synthesis of α-arylglycine derivatives. This operationally simple method utilizes glyoxylic acid, sulfonamides, and arylboronic acids as starting materials to obtain α-arylglycine scaffold in good yields and enantioselectivities. The synthesized products can be directly used as building blocks in peptide synthesis.
FRONTIERS IN CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Juhyun Cho, Jong Hwa Jeong, Hyosun Lee, Jungkyu K. Lee, Saira Nayab
Summary: A series of Cu(II) complexes containing C-1-symmetric thiophene derivatives of (1R,2R)-N1-(naphthalen-2-ylmethyl)cyclohexane-1,2-diamine were synthesized and characterized, demonstrating high yield and excellent enantioselectivity for the desired product. The catalytic systems also showed good activity and moderate to high enantioselectivity for aliphatic aldehydes.
INORGANICA CHIMICA ACTA
(2021)
Article
Chemistry, Organic
Arti Ramani, Rachit S. Patil, Hussain Bhukya, Togati Naveen
Summary: We have developed a novel copper-catalyzed intermolecular alkyl formylation reaction of arene sulfonamides. This method is a significant advancement in the field as it eliminates the need for exogenous acid, base, or oxidant and can be completed within two hours. Various N,N-alkyl formylated sulfonamides were synthesized in moderate to good yields.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Qiaoli Li, Lanting Xu, Dawei Ma
Summary: Direct N-arylation of sulfonamides using a combination of copper and oxalamides (or 4-hydroxypicolinamides) as catalysts is an efficient method. It allows for a wide range of reactions between sulfonamides and (hetero)aryl bromides, and even works well with primary sulfonamides and (hetero)aryl chlorides under the catalysis of Cu2O and a 4-hydroxypicolinamide.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Biochemistry & Molecular Biology
Kosuke Yamamoto, Keisuke Miyamoto, Mizuki Ueno, Yuki Takemoto, Masami Kuriyama, Osamu Onomura
Summary: In this study, glycerol was efficiently transformed into optically active monosulfonylated glycerol using a specific catalyst system. The synthetic utility of the monosulfonylated glycerol was demonstrated by its transformation into a C3 unit with differentially protected three hydroxy moieties.
Article
Chemistry, Multidisciplinary
Yue Jia, Zhihan Zhang, Guo-Ming Yu, Xuan Jiang, Liang-Qiu Lu, Wen-Jing Xiao
Summary: A visible light induced enantioselective deaminative arylation of amino acid derivatives by bifunctional copper catalysis is disclosed. A variety of alpha-aryl-N-phenylamides are prepared with good efficiency and high enantioselectivity. Experimental investigations and theoretical calculations reveal the crucial role of additional phenols in improving catalytic efficiency and enantiocontrol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Chunming Gui, Yuanyuan Peng, Yang Zhou, Yixuan Zheng, Haifeng Wang, Qiongjiao Yan, Hui Zhou, Wei Wang, Fen-Er Chen
Summary: This paper reports the copper-catalyzed asymmetric propargylic substitution reaction, which efficiently synthesizes multifunctionalized products bearing a terminal alkyne unit with good stereoselectivity. The products can also be easily derivatized into other potentially valuable organic compounds, showing great potential for pharmaceutical development.
Article
Chemistry, Multidisciplinary
Jialin Qi, Fang Wei, Shuai Huang, Chen-Ho Tung, Zhenghu Xu
Summary: A new method has been developed for the synthesis of sulfur-containing chiral beta-lactams with two consecutive stereogenic centers using copper(I)-catalyzed asymmetric, three-component interrupted Kinugasa reaction. The key lies in the interception of in situ formed chiral four membered copper(I) enolate intermediate with sulfur electrophiles, resulting in good yields and excellent diastereo- and enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Hao Yan, Haolong Wang, Xincheng Li, Xiaoyi Xin, Chunxiang Wang, Boshun Wan
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Article
Chemistry, Multidisciplinary
Yancheng Hu, Ruxia Yi, Xinzhang Yu, Xiaoyi Xin, Chunxiang Wang, Boshun Wan
CHEMICAL COMMUNICATIONS
(2015)
Article
Chemistry, Multidisciplinary
Fen Xu, Chunxiang Wang, Haolong Wang, Xincheng Li, Boshun Wan
Article
Chemistry, Organic
Xiaodong Lu, Bin Pan, Fan Wu, Xiaoyi Xin, Boshun Wan
TETRAHEDRON LETTERS
(2015)
Article
Chemistry, Organic
Qinglei Chong, Chunxiang Wang, Dongping Wang, Haolong Wang, Fan Wu, Xiaoyi Xin, Boshun Wan
TETRAHEDRON LETTERS
(2015)
Article
Chemistry, Multidisciplinary
Tengfei Li, Fen Xu, Xincheng Li, Chunxiang Wang, Boshun Wan
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2016)
Article
Chemistry, Organic
Tengfei Li, Hao Yan, Xincheng Li, Chunxiang Wang, Boshun Wan
JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Yingying Zhao, Yancheng Hu, Haolong Wang, Xincheng Li, Boshun Wan
JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Yingying Zhao, Haolong Wang, Xincheng Li, Dongping Wang, Xiaoyi Xin, Boshun Wan
ORGANIC & BIOMOLECULAR CHEMISTRY
(2016)
Article
Chemistry, Organic
Yingying Zhao, Yancheng Hu, Chunxiang Wang, Xincheng Li, Boshun Wan
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Yingying Zhao, Yancheng Hu, Xincheng Li, Boshun Wan
ORGANIC & BIOMOLECULAR CHEMISTRY
(2017)
Article
Chemistry, Organic
Hao Yan, Xincheng Li, Chunxiang Wang, Boshun Wan
ORGANIC CHEMISTRY FRONTIERS
(2017)
Article
Chemistry, Organic
Xiaodong Lu, Xiaoyi Xin, Boshun Wan
TETRAHEDRON LETTERS
(2018)
Article
Chemistry, Organic
Songjie Yu, Boshun Wan, Xingwei Li
Article
Chemistry, Applied
Ruxia Yi, Xincheng Li, Boshun Wan
ADVANCED SYNTHESIS & CATALYSIS
(2018)
