Article
Chemistry, Multidisciplinary
Chen Chen, Xing-Xing Yang, Zhi Zhao, Bo Han, Wei Du, Ying-Chun Chen
Summary: In this study, the normal 1,3-dipolar cycloaddition between the carbonates of 4-hydroxy-2-cyclopentenones and C,N-cyclic azomethine imines was switched to an inverse-electron-demand version under Pd(0) catalysis. This transformation was achieved by in situ generation of HOMO-raised eta(2)-Pd(0)-cyclopentadienone complexes. The researchers constructed a variety of fused heterocyclic architectures with high levels of diastereo and enantioselectivity. Furthermore, diastereodivergent synthesis was realized by tuning the bifunctional phosphine ligands. A similar reaction with in situ formed thiophene-1,1-dioxide was also compatible by using a chiral bisphosphine ligand, leading to the formation of fused cyclic sulfone frameworks with high stereoselectivity.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Jing Huang, Bo Jiang, Xiyuan Zhang, Yanfeng Gao, Xiufang Xu, Zhiwei Miao
Summary: A synthetic strategy for accessing functionalized azabicyclo[3.3.1]alkenones with three tertiary stereocenters has been developed. The method is scalable and the products can be transformed to various eight-membered-ring bridged heterocyclic molecules.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Arthur Lebrene, Thomas Martzel, Laura Gouriou, Morgane Sanselme, Vincent Levacher, Sylvain Oudeyer, Carlos Afonso, Corinne Loutelier-Bourhis, Jean-Francois Briere
Summary: A straightforward method for synthesizing original 1,6-diazabicyclo[4.3.0]nonane-2,7-diones was developed using a DBU-organocatalyzed multicomponent Knoevenagel-aza-Michael-Cyclocondensation reaction. Analysis of key reactive intermediates using mass spectrometry confirmed the proposed mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Wu-Lin Yang, Tian-Tian Liu, Tao Ni, Bin Zhu, Xiaoyan Luo, Wei-Ping Deng
Summary: An iridium-catalyzed trifluoroacetic acid-promoted asymmetric cascade allylation/Pictet-Spengler cyclization reaction of azomethine ylides with aromatic allylic alcohols is reported, providing a facile and scalable method for the construction of 1,3,4-trisubstituted tetrahydroisoquinolines containing two stereogenic centers in good yields with generally excellent diastereo- and enantioselectivities. Additionally, a series of aromatic heterocyclefused piperidines were also obtained with excellent enantiocontrol by this methodology.
Article
Biochemistry & Molecular Biology
Ursa Stanfel, Dejan Slapsak, Uros Groselj, Franc Pozgan, Bogdan Stefane, Jurij Svete
Summary: Silica gel-bound Cu(II)-enaminone complexes were prepared and showed promising catalytic activity in CuAIAC reactions, but suffered from poor reusability. Improved reusability was achieved by using a 4-aminobenzoic acid linker attached to the enaminone via an amide bond.
Article
Chemistry, Organic
Junfeng Fu, Ingrid Rakielle Tsapy Takia, Peng Chen, Wei Liu, Chengjun Jiang, Weijun Yao, Xiaofei Zeng, Yongjiang Wang, Xiaoyu Han
Summary: The phosphine-mediated tandem [3 + 2] cyclization/intramolecular Wittig reaction of 3-aroylcoumarin with alkynone allows the synthesis of 2-chromanone-fused bicyclo[3.2.0]heptenones in moderate to high yields with remarkably high regio- and diastereoselectivities under mild reaction conditions, providing an extremely simple, economical, and straightforward synthetic method for constructing complex cyclic building blocks with potential biological applications.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Chemistry, Organic
Giuseppe Faita, Mariella Mella, Paolo Quadrelli
Summary: This review discusses the application of 1,3-dipolar cycloadditions in the design and synthesis of antiviral compounds, focusing on the use of nitrones and nitrile oxides. The products obtained from these reactions showed promising antiviral activities through blocking virus replication.
