Article
Chemistry, Organic
Abhijit Shyam, Amit Kumar Pradhan, Paritosh Mondal
Summary: BACs are newly discovered umpolung catalysts with potential applications in organic synthesis. The mechanism of Et-BAC catalyzed synthesis of 1,4-diketones has been investigated using DFT, revealing its umpolung efficacy. Experimental findings have confirmed the validity of the DFT exploration.
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Wei Li, Jie Lv, Yonggui Robin Chi
Summary: An N-Heterocyclic carbene (NHC) catalyzed aza-benzoin reaction of benzothiazole-2-carboxaldehydes and N-sulfonylimines is reported for the first time, leading to benzothiazole-containing aminoketone products bearing different substituents and substitution patterns in good to excellent yields under mild conditions.
Article
Chemistry, Organic
Pavit Kumar Ranga, Feroz Ahmad, Prashant Nager, Prabhat Singh Rana, Ramasamy Vijaya Anand
Summary: The catalytic application of bis(amino)cyclopropenium ion in conjugate addition reactions has been investigated, with the hydrogen atom on the cyclopropene ring acting as a hydrogen-bond donor catalyst. Experimental studies have verified that the C-H hydrogen in the cyclopropene ring is solely responsible for catalyzing these transformations, activating the carbonyl group of p-quinone methide through hydrogen bonding.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Polymer Science
Xingxing Zeng, Anlin Zhang, Chaoshui Liu, Jia Cheng, Minghua Hu
Summary: Novel polyether-immobilized aza-bis(oxazolines) ligands with stable helical conformation and controllable molecular weights were prepared by anionic polymerization. The asymmetric Henry reactions demonstrated a relationship between the helical conformation of these polyethers and their catalytic activity, giving high yields and enantiomeric excess. These helical polyether-immobilized chiral ligands can be easily recycled without losing their enantioselectivity.
EUROPEAN POLYMER JOURNAL
(2023)
Article
Chemistry, Physical
Hao Liu, Pengyu He, Xuanlong Liao, Yipeng Zhou, Xingkuan Chen, Wenpiao Ou, Zhenhong Wu, Cong Luo, Limin Yang, Jianfeng Xu
Summary: This study reports an organocatalytic desymmetrization strategy for constructing optically active silicon-stereogenic silacycles. The strategy enables the selective synthesis of organosilicon compounds with carbon and silicon-stereogenic centers.
Article
Chemistry, Organic
Julia O. Strelnikova, Alexander N. Koronatov, Nikolai Rostovskii, Alexander F. Khlebnikov, Olesya Khoroshilova, Mariya A. Kryukova, Mikhail S. Novikov
Summary: The domino reaction catalyzed by Rh-2(Piv)(4) leads to the formation of N-sulfonylated (Z)-2-(2-aminovinyl)imidazoles, providing a direct and flexible access to the desired compounds.
Article
Chemistry, Multidisciplinary
Hui Hu, Zhaobin Wang
Summary: This method provides a modular and efficient approach to accessing diverse chiral ss-amino alcohols bearing vicinal stereocenters, using a chiral chromium catalyst with chemoselective single-electron reduction of imines, fast radical interception, and selective addition to aldehydes.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Hui Hu, Zhaobin Wang
Summary: Chiral ss-amino alcohols are important structural motifs in pharmaceuticals, natural products, and asymmetric catalysis. The development of catalytic approaches to access ss-amino alcohols bearing vicinal stereocenters from readily available chemicals is a challenge. In this study, a Cr-catalyzed asymmetric cross aza-pinacol coupling of aldehydes and N-sulfonyl imines is described. A chiral chromium catalyst plays a triple role in this protocol, enabling chemoselective single-electron reduction of the imine, fast radical interception to inhibit radical addition to imines, and chemo- and stereoselective addition to aldehydes instead of imines.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Physical
Fachao Yan, Zijun Huang, Chen-Xia Du, Jian-Fei Bai, Yuehui Li
Summary: The FeI2-catalyzed reductive Strecker type reaction of formamides was reported, which successfully produced amino acetonitriles instead of aldehydes with higher yields than Ir or Rh catalysts. This method demonstrated the ability to one-pot construct complex molecules and conveniently produce homologated carboxylic acids from aldehydes.
JOURNAL OF CATALYSIS
(2021)
Article
Chemistry, Organic
Wen-Kang Wang, Fei-Yun Bao, Si-Tian Wang, Sheng-Yin Zhao
Summary: A method for preparing 3-aminomethylated maleimides via Morita-Baylis-Hillman (MBH) reaction was developed. This study used maleimides and 1,3,5-triazinanes as substrates, and through the phosphine-catalyzed coupling, a series of 3-aminomethylated maleimide derivatives were obtained with a yield of 41-90%. Acylation, isomerization, and Michael addition reactions demonstrated the synthetic application of this method. Control experiments revealed that phosphorus ylide formation and elimination occur during the reaction pathway.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yangyang Wang, Xiaoming Huang, Haojie Ji, Hongwei Zhou, Hongjie Gao, Jianfeng Xu
Summary: A quinine-derived thiourea-promoted enantioselective aza-Friedel-Crafts reaction of 3-aminobenzofurans with isatin-derived ketimines was developed, providing a variety of 3-benzofuran-3-amino-2-oxindoles bearing a quaternary stereocenter with good to excellent yields and moderate to excellent enantioselectivities. The synthetic potential of this concise and efficient protocol was demonstrated by gram-scale preparation and further transformation of the adduct to an optically pure spirocyclic oxindole.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Li Jing, Zhong-Jun Li, Er-Qing Li
Summary: We have developed a new 1,3-bis-electrophilic motif and applied it in palladium-catalyzed (3 + 2) annulations. This method offers a straightforward approach to constructing functionalized pyrrolidines with good yields. Importantly, the configuration (Z/E) of the 1,3-bis-electrophilic motif does not affect the yield and chemoselectivity of the reaction. Furthermore, preliminary asymmetric investigations using Pd(0)/thiourea synergistic catalysis resulted in moderate enantioselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Daniel Sowa Prendes, Florian Papp, Nagesh Sankaran, Nardana Sivendran, Frederike Beyer, Christian Merten, Lukas J. Goossen
Summary: Arylglycines, which are important pharmacophores in several top-selling drugs, can now be synthesized from abundant aryl chlorides using a Pd-catalyzed Schollkopf-type amino acid synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Jing Li, Zhonglin Wei, Jungang Cao, Dapeng Liang, Yingjie Lin, Haifeng Duan
Summary: A highly enantioselective aza-Friedel-Crafts reaction of 1H-indoles with isatin-derived N-Cbz-ketimines catalyzed by quinine-derived phase-transfer catalysts was developed. Chiral 3-aminobisindole compounds containing a tetrasubstituted stereocenter were constructed in high yields (82-91%) and moderate to excellent enantioselectivities (46-94% ee).
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Ryoya Tajima, Takaaki Saito, Takayoshi Arai
Summary: The conventional acid-catalyzed aza-Friedel-Crafts reaction of phenols with imines typically shows ortho-selectivity. However, a chiral bis(imidazolidine) pyridine (PyBidine)-Ni(OAc)(2) catalyst can switch the regioselectivity to para-selectivity. This switch is facilitated by the bulky PyBidine-Ni(OAc)(2) catalyst with a Ph2CHCH2 substituent, resulting in highly para-selective aza-Friedel-Crafts reactions (up to 99:1 para/ortho selectivity).
Article
Chemistry, Organic
Steven M. Langdon, Claude Y. Legault, Michel Gravel
JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Organic
Pouyan Haghshenas, J. Wilson Quail, Michel Gravel
JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Yunus E. Turkmen, Michel Gravel, Viresh H. Rawal
JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Pouyan Haghshenas, Michel Gravel
Article
Chemistry, Organic
Pouyan Haghshenas, Steven M. Langdon, Michel Gravel
Article
Chemistry, Multidisciplinary
Myron M. D. Wilde, Michel Gravel
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2013)
Article
Chemistry, Organic
Sida Zhou, Eduardo Sanchez-Larios, Michel Gravel
JOURNAL OF ORGANIC CHEMISTRY
(2012)
Article
Chemistry, Multidisciplinary
Steven M. Langdon, Myron M. D. Wilde, Karen Thai, Michel Gravel
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2014)
Article
Chemistry, Organic
Karen Thai, Steven M. Langdon, Francois Bilodeau, Michel Gravel
Article
Chemistry, Organic
Venkata Krishna Rao Garapati, Michel Gravel
Article
Chemistry, Multidisciplinary
Myron Wilde, Danielle Arzur, Blandine Baratte, Dorian Lefebvre, Thomas Robert, Thierry Roisnel, Catherine Le Jossic-Corcos, Stephane Bach, Laurent Corcos, William Erb
NEW JOURNAL OF CHEMISTRY
(2020)