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, Multidisciplinary
Daniel Rozsar, Alistair J. M. Farley, Iain McLauchlan, Benjamin D. A. Shennan, Ken Yamazaki, Darren J. Dixon
Summary: This article describes the enantioselective intermolecular conjugate addition of nitroalkanes to unactivated alpha,beta-unsaturated esters catalyzed by a bifunctional iminophosphorane (BIMP) superbase. It provides a straightforward approach to the synthesis of pharmaceutically relevant enantioenriched gamma-nitroesters with unprecedented selectivity. The methodology demonstrates broad substrate scope and has been successfully applied on a gram scale with reduced catalyst loading, allowing for catalyst recovery.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Shuting Tan, Jian-Guo Liu, Ming-Hua Xu
Summary: A rhodium-catalyzed asymmetric 1,4-addition reaction provides a practical approach for synthesizing highly enantioenriched chiral N-alkylindoles.
Article
Chemistry, Applied
Yuan Chen, Rui Yu, Min Wang, Yanmin Huang, Yungui Peng
Summary: An asymmetric 1,6-conjugate addition reaction of dialkyl diazomethylphosphonates to para-quinone methides was developed using phase-transfer catalysis, yielding chiral diarylmethylated diazomethylphosphonates with high yields and enantioselectivities. The resulting products were further transformed into bioactive compounds with diarylmethine stereogenic centers.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
David A. Gutierrez, James Fettinger, K. N. Houk, Kaori Ando, Jared T. Shaw
Summary: This study describes the Lewis-acid-promoted addition of prochiral E- and Z-allyl nucleophiles to chiral alpha-alkoxy N-tosyl imines with stereochemical control, resulting in the synthesis of two isomers of clausenamide.
Article
Chemistry, Organic
Yingying Ren, Qishun Yu, Chengrong Lu, Bei Zhao
Summary: The catalytic enantioselective Michael addition of α,β-unsaturated ketones with malononitrile was successfully achieved using rare-earth metal amides and chiral phenoxy-functionalized TsDPEN ligands. The optimal reaction conditions provided the desired products in excellent yields and good to high enantioselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Won Jun Jang, Jeongkyu Woo, Jaesook Yun
Summary: The study reported a method to synthesize enantioenriched alkylboron compounds through conjugate addition, which are influenced by two contiguous carbon stereogenic centers, with high yield and enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Congzheng Gu, Guangzheng Tian, Qingyu Yin, Fan Wu, Zhiming Li, Xiaoyu Wu
Summary: An enantioselective Mannich addition reaction of 3,5-disubstituted 4-nitroisoxazoles to beta,gamma-alkynyl-alpha-ketimino esters has been developed using an amide phosphonium salt-based catalyst. Chiral tertiary propargylic amine products were obtained with moderate to good yields and enantioselectivities.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Applied
Brigita Mudrakova, Peter Kisszekelyi, Denisa Vargova, Dorota Zakiewicz, Radovan Sebesta
Summary: This paper presents a highly enantio- and diastereoselective tandem transformation method, using Cu-catalyzed conjugate addition of Grignard reagents to heterocyclic Michael acceptors, followed by one-pot trapping of in situ formed enolates with stabilized carbocations or their equivalents. This method allows the installation of structurally attractive substituents on heterocyclic compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Junwen Wang, Jun Li, Yan Wang, Sisi He, Hengzhi You, Fen -Er Chen
Summary: In this study, a polymer-supported chiral heterogeneous copper catalyst was reported, which demonstrated high reactivity and enantioselectivity in asymmetric conjugate addition reactions.
Article
Chemistry, Multidisciplinary
Jinbin Zhu, Zhenyue Li, Jiaqi Li, Duanshuai Tian, Ronghua Xu, Zhiyong Tan, Zhengwang Chen, Wenjun Tang
Summary: In this report, an efficient rhodium-catalyzed addition of arylboronic acids to N-heteroaryl ketones is established, affording a variety of valuable alpha-heteroaryl alcohols with excellent functional group compatibility. The employment of the WingPhos ligand containing two anthryl groups is crucial for this transformation.
Article
Chemistry, Organic
Ping Zhang, Guo-Li Chai, En-Ze Yao, Li-Xiao Guo, Xue-Yu Liu, Junbiao Chang
Summary: Asymmetric conjugate addition of organic boronic acids to dienones was achieved using chiral catalysts, resulting in high yields of enantiopure bis-adducts with excellent chemoselectivities and enantioselectivities. These catalytic systems demonstrated high efficiency and broad substrate scope.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Yu-Chao Wang, Zhao-Xin Xiao, Miao Wang, Shao-Qian Yang, Jin-Biao Liu, Zhi-Tao He
Summary: This study presents modular protocols for 1,5-conjugate addition reactions via palladium hydride catalysis, which has been considered unfeasible. The results show that the 1,5-conjugate addition products can be conveniently transformed into various privileged enantioenriched motifs, indicating the potential applications of this method in synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Benat Lorea, Ane Garcia-Urricelqui, Josee M. Odriozola, Jesus Razkin, Maialen Espinal-Viguri, Mikel Oiarbide, Antonia Mielgo, Jesus M. Garcia, Claudio Palomo
Summary: The direct asymmetric conjugate addition of unactivated α-branched nitroalkanes can be achieved using chiral amine/ureidoaminal bifunctional catalysts and a tunable acrylate template, resulting in tertiary nitrocompounds with high enantioselectivity. Elaboration of the ketol moiety allows for the preparation of various derivatives, including carboxylic acids, aldehydes, nitriles, and enantioenriched 5,5-disubstituted γ-lactams.
Article
Chemistry, Multidisciplinary
Chihiro Homma, Taichi Kano, Keiji Maruoka
Summary: A bifunctional amino sulfonamide-catalyzed asymmetric conjugate addition of aldehydes to alkenyl alkynyl ketimines has been developed, yielding the desired conjugate adducts with high chemo-, diastereo- and enantioselectivity.
CHEMICAL COMMUNICATIONS
(2021)