Article
Chemistry, Multidisciplinary
Guang-Jian Mei, Jonathan J. Wong, Wenrui Zheng, Anjanay A. Nangia, K. N. Houk, Yixin Lu
Summary: The first catalytic asymmetric synthesis of N-N axially chiral compounds has been achieved, adding a new dimension to axially chiral molecules and atropisomerism. DFT calculations have been used to understand enantioselectivity and guide the design of similar molecules. Research on N-N axial atropisomerism holds promise for new discoveries in medicinal chemistry and asymmetric catalysis.
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, Organic
Yongbiao Guo, Zhenhua Gao, Junchen Li, Xiaojing Bi, Enxue Shi, Junhua Xiao
Summary: This study presents a highly efficient and practical method for the direct synthesis of 2,3-dihydroquinazolinones from diverse aldehydes with excellent yields and enantioselectivity. The method shows improved enantioselectivity for aliphatic aldehydes and wide tolerance to different functional groups. Gram-scale synthesis and simplified work-up procedure demonstrate the practicality of this method.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jin Huang, Guang-xun Li, Gao-feng Yang, Ding-qiang Fu, Xiao-kang Nie, Xin Cui, Jin-zhong Zhao, Zhuo Tang
Summary: N-Substituted tetrahydroquinoxalines were efficiently synthesized in good yield and enantioselectivity using readily available substrates. The reaction involves a regioselective Heyns rearrangement/enantioselective transfer hydrogenation in one pot, and both the substrate scope and reaction mechanism were systematically investigated.
Article
Chemistry, Multidisciplinary
Deyun Qian, Srikrishna Bera, Xile Hu
Summary: A nickel-catalyzed hydroalkylation method has been developed to assemble a wide range of chiral alkyl amines with high regio- and enantioselectivity from enecarbamates and alkyl halides. The method is suitable for both nonactivated and activated alkyl halides, producing enantiomerically enriched amines with high functional group tolerance.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Sooyun Choi, Melody C. Guo, Gavin M. Coombs, Scott J. Miller
Summary: An atroposelective synthesis method for N-aryl 1,2,4-triazoles was developed. By utilizing a chiral phosphoric acid catalyst, a cyclodehydration reaction achieved asymmetric induction, resulting in atropisomeric N-aryl 1,2,4-triazoles with up to 91:9 enantiomeric ratio. Further crystallization of the isolated heterocycle enhanced the atropisomeric ratio of several analogs to 99:1 or higher. Additionally, a divergent and substrate-dependent reaction pathway leading to a different heterocyclic product was revealed.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Supattra Somsri, Banyong Suwankaisorn, Krissanapat Yomthong, Wanmai Srisuwanno, Sorasak Klinyod, Alexander Kuhn, Chularat Wattanakit
Summary: Enantioselective catalysis is crucial in modern chemistry and pharmaceutical science. In this study, nanostructured metal layers imprinted with chiral information were developed as catalysts for the asymmetric synthesis of pharmaceutical compounds. The designed materials were successfully used as catalytically active stationary phases for continuous asymmetric flow synthesis. This work demonstrates the potential of producing real chiral pharmaceuticals at nanostructured metal surfaces.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Cong-Shuai Wang, Qi Xiong, Hui Xu, Hao-Ran Yang, Yanfeng Dang, Xiu-Qin Dong, Chun-Jiang Wang
Summary: A novel organocatalytic method for the synthesis of axially chiral N,N'-pyrrolylindoles based on o-alkynylanilines has been successfully developed using chiral phosphoric acid as the catalyst. This strategy allows for the efficient and selective synthesis of N,N'-pyrrolylindoles with excellent yields and enantioselectivity. Preliminary biological activity studies show that these compounds exhibit promising cytotoxicity against various cancer cell lines.
Article
Chemistry, Organic
Yi Li, Wang-Yuren Li, Xiaoxue Tang, Xiaohua Liu, Xiaoming Feng
Summary: The establishment of an asymmetric Heine reaction and the synthesis of a library of pyridine-oxazolines demonstrate the potential of these compounds as chiral ligands and Lewis base catalysts. A possible reaction mechanism was proposed based on control experiments.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Hanyang Bao, Yunrong Chen, Xiaoyu Yang
Summary: In this study, a highly efficient catalytic asymmetric synthesis of diaryl ether atropisomers was reported via an organocatalyzed enantioselective desymmetrization protocol. The chiral phosphoric acid-catalyzed asymmetric electrophilic aromatic aminations of symmetrical substrates provided a series of diaryl ether atropisomers with excellent yields and enantioselectivities. The utilization of the 1,2-benzenediamine moiety in the products allowed for the facile construction of heterocycles, leading to a wide range of structurally diverse and novel azaarene-containing diaryl ether atropisomers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Changkai Wang, Jiangtao Sun
Summary: An efficient method for the synthesis of bipyrroles with an axially chiral N-N bond has been developed using a rhodium-catalyzed C-H bond insertion reaction. The desired atropisomers were obtained in high yields (up to 97%) and with excellent enantioselectivities (up to 99% ee).
Article
Chemistry, Organic
Jiaoyang Wang, Danfeng Wang, Xiaofeng Tong
Summary: The MnO2-promoted oxidative coupling process reported in this study provides a mild and scalable method for the synthesis of trisubstituted hydrazine. This new approach is operationally straightforward and can be easily scaled up.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Bowen Li, Dan Liu, Yanhua Hu, Jianzhong Chen, Zhenfeng Zhang, Wanbin Zhang
Summary: An efficient nickel-catalyzed asymmetric hydrogenation of hydrazones to chiral hydrazines has been achieved with high yields and enantiomeric excess. Deuterium labelling experiments showed tautomerization of hydrazone substrates in mixed solvents, while the presence of acids promoted the dissociation of the active nickel catalyst in the catalytic cycle.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Multidisciplinary Sciences
Shan Wang, Jian-Xin Zhang, Tian-Yi Zhang, Huan Meng, Bi-Hong Chen, Wei Shu
Summary: Chiral aliphatic amine and alcohol derivatives are difficult to access due to the challenge to differentiate between spatially and electronically similar alkyl groups. By utilizing a nickel-catalyzed enantioselective hydroalkylation, enantioenriched alpha-branched aliphatic acyl amines and esters can be efficiently synthesized with good yields and excellent enantioselectivity.
NATURE COMMUNICATIONS
(2021)
