Article
Chemistry, Organic
Kai Zhou, Ming Bao, Hongkai Sha, Guizhi Dong, Kemiao Hong, Xinfang Xu, Wenhao Hu
Summary: A Rh-catalyzed diastereoselective three-component reaction has been developed for the efficient synthesis of vicinal diamine derivatives with two tertiary stereocenters in high yields (75%->95%) and high to excellent diastereoselectivities. The generated product can be easily converted to free diamines via hydrolysis of the imine motif under mild conditions.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Yu Zheng, Zhu-Jun Wang, Zhi-Peng Ye, Kai Tang, Zhen-Zhen Xie, Jun-An Xiao, Hao-Yue Xiang, Kai Chen, Xiao-Qing Chen, Hua Yang
Summary: A metal-free photosensitized protocol for regioselective diamination of alkene feedstocks was developed. The reaction proceeds in a single step and yields differentially protected 1,2-diamines in moderate to high yields. Mechanistic studies reveal that the excellent regioselectivity is due to the large reactivity difference between two different N-centered radical species.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Byung Joo Lee, Andrew R. Ickes, Anil K. Gupta, Seth C. Ensign, Tam D. Ho, Anika Tarasewicz, Evan P. Vanable, Gregory D. Kortman, Kami L. Hull
Summary: In this study, the rhodium-catalyzed hydroamination of allyl amine derivatives using various amine nucleophiles was presented. This methodology provides a powerful approach for the synthesis of unsymmetrical vicinal diamines and has been demonstrated to be useful in the rapid synthesis of bioactive molecules and analogs.
Article
Chemistry, Organic
Jie Cao, Daqi Lv, Fei Yu, Mong-Feng Chiou, Yajun Li, Hongli Bao
Summary: The vicinal diamine motif is important in natural products, drug design, and organic synthesis, and developing methods for synthesizing vicinal diamines has long been of interest. This study reports on a regioselective intermolecular three-component vicinal diamination reaction using styrenes, acetonitrile, and azodicarboxylates. The diamination products can be obtained in moderate to excellent yields via the Ritter reaction, and synthetic applications and theoretical studies of this reaction have been conducted.
Article
Chemistry, Organic
Martin Kamlar, Elin Henriksson, Ivana Cisarova, Marcus Malo, Henrik Sunden
Summary: This study successfully synthesized compounds with a specific structure using a special reaction method, providing a promising synthetic building block for further synthetic applications.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Lei Zhang, Chengyu Liu, Maolin Sun, Chaoming Liang, Liming Cao, Xiantong Yao, Yueyue Ma, Ruihua Cheng, Jinxing Ye
Summary: An iridium catalytic system using a ferrocene-based phosphine ligand with a modular and tunable unsymmetrical vicinal diamine scaffold was developed for the asymmetric hydrogenation of aryl ketones. This method provided a powerful tool for the enantioselective synthesis of diverse chiral alcohols, exhibiting excellent reactivity and enantioselectivity (yield up to 99%, ee up to 99%, and turnover number up to 50,000). The substituents and chirality of unsymmetrical diamines in the ligands played a crucial role in achieving satisfactory results.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Hui-Jie Pan, Yamei Lin, Taotao Gao, Kai Kiat Lau, Wei Feng, Binmiao Yang, Yu Zhao
Summary: This study presents an unprecedented diastereoconvergent synthesis of vicinal diamines from diols, using an economical and redox-neutral process. Efficient and diastereoselective coupling of readily available anilines and 1,2-diols under cooperative ruthenium and Lewis acid catalysis was achieved, along with the first enantioconvergent double amination of racemic 1,2-diols through an effective chiral iridium/phosphoric acid co-catalyzed procedure, leading to practical access to highly valuable enantioenriched vicinal diamines.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Yongzhuo Xu, Boqiang Wang, Jiajia Wang, Xuan Zhou, Jiaxing Chen, Xinjia Guo, Guo-Jun Deng, Wen Shao
Summary: In this study, a simple method for the synthesis of 2-azidoimines through azidoamination reactions was reported. The synthetic potential of the method was further demonstrated through sequential condensation/amination reactions and chemoselective, orthogonal transformations, leading to the access of biologically active unsymmetrical diamines.
Article
Chemistry, Multidisciplinary
Mingkang Zhou, Yaodong Lin, Xiao-Xuan Chen, Guangqing Xu, Lung Wa Chung, Wenjun Tang
Summary: We report the chiral diboron-templated asymmetric homocoupling of aryl alkyl ketimines, leading to the formation of chiral vicinal tetrasubstituted diamines with high enantioselectivities and good to high yields. This powerful and efficient reaction is achieved by rational design and engineering of chiral diborons, which participate in a [3,3]-sigmatropic rearrangement. DFT studies reveal that different conformational assembling strategies of chiral diborons ensure the excellent enantioselectivity in the tight concerted transition states.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Kwihwan Park, Shinichi Furusato, Chikara Furugen, Takashi Ikawa, Tsuyoshi Yamada, Hironao Sajiki
Summary: In this study, a solvent-free ruthenium-on-carbon-catalyzed hydrogenation reaction of CBDK was developed for the production of cis-CBDO, and the reaction mechanism for cis-selectivity was proposed based on density functional theory (DFT) calculations.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Chao Wu, Baode Ma, Gen-Qiang Chen, Xumu Zhang
Summary: In this study, an efficient synthetic method for chiral beta-heteroaryl amino alcohols was developed. The reaction showed high enantioselectivity and yield, and was successfully used for the gram-scale synthesis of important intermediates.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Lisi Yuan, Ya Fang, Zhaobo Zhou, Tinghong Lv, Yingpeng Su, Jian Liu, Xiaolei Wang
Summary: This Letter describes a highly diastereoselective synthesis method for C-hydroxymethine glycosides from glycal anomers using an achiral N-heterocyclic carbene-copper catalyst. The diastereoselectivity is controlled by both the stereocenter of the substrate and the chirality of the N-heterocyclic carbene-copper complex, independent of the stereochemistry of C5 and the anomeric position. This approach allows for the production of a diverse range of C-hydroxymethine glycosides using versatile glycals and various functionalized aldehydes.
Article
Chemistry, Multidisciplinary
Sopon Butcha, Veronique Lapeyre, Chularat Wattanakit, Alexander Kuhn
Summary: In modern chemistry, chiral (electro)catalysis is a crucial strategy for producing enantiomerically pure compounds. However, uncontrollable stereochemistry due to side reactions remains a challenge for chiral catalysis. This study proposes a synergetic combination of two strategies: the design of mesoporous Pt films with chiral recognition sites, and the controlled formation of a self-assembled monolayer. By selectively functionalizing the electrode's surface with a monolayer of organosulfur ligands, undesired side reactions are significantly suppressed, leading to an increase in enantiomeric excess to over 90% in the context of enantioselective electrosynthesis. This strategy also greatly reduces the total reaction time. Overall, this study opens up promising possibilities for the development of heterogeneous enantioselective electrocatalysis strategies.
Article
Chemistry, Physical
Huiyu Zhang, Han Han, Linfei Xiao, Wei Wu
Summary: This study prepared a series of CoMoCx catalysts using ionic liquids as precursors and optimized the efficiency of CO2 hydrogenation to ethanol by adjusting the carburization temperature. The results showed high ethanol selectivity and yield under optimal reaction conditions.
Article
Chemistry, Physical
Jiang Wang, Xin Lin, Pan-Lin Shao, Jingyuan Song, Jialin Wen, Xumu Zhang
Summary: This study presents an Rh/DuanPhos-catalyzed double asymmetric hydrogenation of alpha-iminoketones for accessing chiral vicinal amino alcohols. The methodology offers advantages such as one-pot operation, high efficiency, operational simplicity, limited waste, broad reaction scope, and high yields and stereoselectivities. Furthermore, the mechanism of the transformation was revealed to be a stepwise reaction by isolating and analyzing reaction intermediates.
