Article
Chemistry, Organic
Xiaolei Ji, Chaoren Shen, Xinxin Tian, Kaiwu Dong
Summary: A palladium-catalyzed asymmetric hydroesterification reaction was developed for preparing chiral alpha-substituted succinates with moderate yields and high ee values. The kinetic profile of the reaction progress indicated that the alkene substrate underwent hydroesterification followed by esterification with alcohol. The enantioselectivity was elucidated by density functional theory computation.
Article
Chemistry, Organic
Chao Dong, Dao-Sheng Liu, Lei Zhang, Xiang-Ping Hu
Summary: An enantioselective Rh-catalyzed hydrogenation of E/Z mixtures of trisubstituted vinyl esters has been achieved using a chiral ferrocenylphosphine-phosphoramidite ligand. The reaction showed high yields and good to high enantioselectivities, with the presence of a small amount of t-butanol benefiting the hydrogenation outcome.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Ze Wang, Xianghua Zhao, Shiliang Wang, An Huang, Yifan Wang, Jiaying He, Fei Ling, Weihui Zhong
Summary: The asymmetric hydrogenation catalyzed by iridium/f-diaphos L1, L5 or L12 was successfully demonstrated for the first time, affording chiral alcohols with high conversions and moderate to excellent enantioselectivities. The protocol could be easily scaled up to gram-scale with a Turnover Number (TON) of 9700.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Wendy L. Williams, Neyci E. Gutierrez-Valencia, Abigail G. Doyle
Summary: This paper reports the first branched-selective cross-coupling of 2-alkyl aziridines with aryl iodides using a Ti/Ni dual-catalytic system. The study demonstrates the tolerance towards functional groups and the effect of the steric and electronic profile on reactivity, resulting in predictive reactivity models and insights into the mechanism.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Multidisciplinary Sciences
Jie Wang, Wei-Feng Zheng, Xue Zhang, Hui Qian, Shengming Ma
Summary: This study reports the synthesis of non-readily available enantioenriched tetrasubstituted allenes through rhodium-catalyzed reactions controlled by steric hindrance. Detailed mechanistic experiments and density functional theory studies reveal the mechanism behind the formation of different stereochemistry under different reaction conditions. A stereodivergent protocol to construct the enantiomer of optically active tetrasubstituted allenes from the same starting materials is successfully developed based on these mechanistic understandings.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Chihiro Homma, Aika Takeshima, Taichi Kano, Keiji Maruoka
Summary: This study demonstrated a highly diastereodivergent synthesis of beta-amino aldehydes with a chiral alpha-tert-amine moiety, utilizing less-activated Z-ketimines in amine-catalyzed Mannich reactions with aldehydes. This method overcame the limitations of structural variations in ketimines, achieving high diastereoselectivity.
Article
Chemistry, Multidisciplinary
Yunnan Xu, Yicong Luo, Jianxun Ye, Delong Liu, Wanbin Zhang
Summary: Novel axially chiral biphenyl diphosphine ligands E-n(m)-BridgePhos have been developed and successfully applied in the Rh-catalyzed enantioselective desymmetric hydrogenation, providing chiral compounds with high yields and excellent enantioselectivities, which serve as vital intermediates for the synthesis of analogues of chiral spirobenzylisoquinoline alkaloids.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Peng Ji, Jing Chen, Xiang Meng, Feng Gao, Yue Dong, Hang Xu, Wei Wang
Summary: This study reports a new method for the synthesis of chiral quaternary alpha-aryl amino acid derivatives. The method involves a photoredox catalytic asymmetric Giese-type reaction and Clayden rearrangement, offering a reliable source for the assembly of highly demanding chiral building blocks.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Xiaofeng Li, Pingping He, Peng Zhu, Yinhong Tang, Yungui Peng
Summary: A method for desymmetrizing asymmetric ring expansion of 4-substituted cyclohexanones with alpha-diazomethylphosphonates catalyzed by a chiral boron Lewis acid has been developed. The method affords beta-ketophosphonate compounds bearing a stereogenic center at the alpha-position in up to 80% yields, 86% ee, and >20 : 1 dr. The obtained products can be further derivatized, demonstrating the synthetic potential of this reaction.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Yin Zheng, Suihan Zhang, Kam-Hung Low, Weiwei Zi, Zhongxing Huang
Summary: This study reports a reductive desymmetrization of halomalonic esters using dinuclear zinc catalysts. The resulting α-halo-β-hydroxyesters serve as important intermediates for the synthesis of drug analogs and polyhalogenated monoterpenes.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Hu Tian, Hong-Ming Zhang, Liang Yin
Summary: In this article, a copper(I)-catalyzed asymmetric conjugate addition/protonation with selenols and alpha-substituted alpha,beta-unsaturated thioamides is described, which produces a series of chiral selenides with high to excellent enantioselectivity. The reaction shows a broad substrate scope for both selenols and alpha-substituted alpha,beta-unsaturated thioamides. The catalytic system is also successfully used for asymmetric selenation of beta-substituted alpha,beta-unsaturated thioamides. A [Cu-(R,R-P)-TANIAPHOS]-SePh species is identified by Se-77 NMR spectra, with a chemical shift at delta 462 ppm. Furthermore, a {[Cu-(R)-TOL-BINAP]-SePh}(2) species is characterized by X-ray analysis, confirming the formation of Cu-Se bond in the reaction. Finally, the straightforward transformations of the thioamide group to amine and thioester are demonstrated.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Cece Wang, Lu Zhou, Jian Qiu, Kai Yang, Qiuling Song
Summary: This paper presents a diastereoselective addition of arylboronic acids to alpha-keto N-tert-butanesulfinyl aldimines catalyzed by a Rh(i) catalyst, offering a practical method to obtain valuable chiral alpha-amino ketones with excellent diastereoselectivity. The reaction is characterized by operational simplicity, mild reaction conditions, and a broad substrate scope.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Hanlin Wei, Hao Chen, Jianzhong Chen, Ilya D. D. Gridnev, Wanbin Zhang
Summary: In this study, an efficient earth-abundant transition-metal nickel catalyzed asymmetric hydrogenation of chiral ethylphosphine products was reported. The products were obtained with up to 99% yield, 96% ee (enantiomeric excess) (99% ee, after recrystallization) and 1000 S/C (substrate/catalyst) ratio. This is also the first study on the asymmetric hydrogenation of terminal olefins using a nickel catalyst under a hydrogen atmosphere. Deuterium-labelling experiments and calculations revealed that the two added hydrogen atoms in the products came from hydrogen gas. Additionally, it was suggested that the reaction involves a Ni-II rather than Ni-0 cyclic process based on the weak attractive interactions between the Ni catalyst and terminal olefin substrate.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Yu Nie, Qianjia Yuan, Feng Gao, Masahiro Terada, Wanbin Zhang
Summary: An efficient iridium-catalyzed double asymmetric hydrogenation of 2,5-dialkylienecyclopentanones is reported, delivering chiral 2,5-disubstituted cyclopentanones in excellent yields and stereoselectivities. The results suggest that the two C=C bonds were hydrogenated in a stepwise manner and the second stereocenter was controlled by the chiral catalyst and the chirality of monohydrogenated product. The hydrogenated products can be prepared on a gram-scale and are easily derivatized.
Article
Chemistry, Organic
Yu Nie, Qianjia Yuan, Feng Gao, Masahiro Terada, Wanbin Zhang
Summary: Herein, we report an efficient iridium-catalyzed double asymmetric hydrogenation of 2,5-dialkylienecyclopentanones, delivering the chiral 2,5-disubstituted cyclopentanones in excellent yields and stereoselectivities. The results of the kinetic experiments and control experiments indicated that the two C=C bonds were hydrogenated in a stepwise manner and the second stereocenter was synergistically controlled by the chiral catalyst and the chirality of monohydrogenated product. The hydrogenated products can be prepared on a gram-scale and are easily derivatized.
Article
Chemistry, Applied
Jian Li, Yin-Long Li, Nan Jin, Ai-Lun Ma, Ya-Nan Huang, Jun Deng
ADVANCED SYNTHESIS & CATALYSIS
(2015)
Article
Chemistry, Organic
Yin-Long Li, Jian Li, Ai-Lun Ma, Ya-Nan Huang, Jun Deng
JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Organic
Yin-Long Li, Jian Li, Sheng-Nan Yu, Ji-Bo Wang, Yan-Min Yu, Jun Deng
Article
Chemistry, Organic
Xiao-Na Wang, Zhi-Xiong Ma, Jun Deng, Richard P. Hsung
TETRAHEDRON LETTERS
(2015)
Article
Chemistry, Multidisciplinary
Gaoyuan Ma, Jun Deng, Mukund P. Sibi
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2014)
Article
Chemistry, Organic
John B. Feltenberger, Changhong Ko, Jun Deng, Sunil K. Ghosh, Richard P. Hsung
Article
Chemistry, Organic
Kyle A. DeKorver, Whitney L. Johnson, Yu Zhang, Richard P. Hsung, Huifang Dai, Jun Deng, Andrew G. Lohse, Yan-Shi Zhang
JOURNAL OF ORGANIC CHEMISTRY
(2011)
Article
Chemistry, Organic
Xiang Zhang, Daisy Zhang-Negrerie, Jun Deng, Yunfei Du, Kang Zhao
JOURNAL OF ORGANIC CHEMISTRY
(2013)
Article
Chemistry, Organic
Jinglei Lv, Daisy Zhang-Negrerie, Jun Deng, Yunfei Du, Kang Zhao
JOURNAL OF ORGANIC CHEMISTRY
(2014)
Article
Chemistry, Organic
Dao-Yong Wang, Xiang-Ping Hu, Chuan-Jin Hou, Jun Deng, Sai-Bo Yu, Zheng-Chao Duan, Jia-Di Huang, Zhuo Zheng
Article
Chemistry, Organic
Jun Deng, Richard P. Hsung, Changhong Ko
Article
Chemistry, Inorganic & Nuclear
Min Qiu, Dao-Yong Wang, Xiang-Ping Hu, Jia-Di Huang, Sai-Bo Yu, Jun Deng, Zheng-Chao Duan, Zhuo Zheng
TETRAHEDRON-ASYMMETRY
(2009)
Article
Chemistry, Inorganic & Nuclear
Zheng-Chao Duan, Xiang-Ping Hu, Jun Deng, Sai-Bo Yu, Dao-Yong Wang, Zhuo Zheng
TETRAHEDRON-ASYMMETRY
(2009)
Article
Chemistry, Inorganic & Nuclear
Chuan-Jin Hou, Wei-Lei Guo, Xiang-Ping Hu, Jun Deng, Zhuo Zheng
TETRAHEDRON-ASYMMETRY
(2011)