Article
Chemistry, Organic
Ricardo Molina Betancourt, Phannarath Phansavath, Virginie Ratovelomanana-Vidal
Summary: Enantioenriched cis-3-fluoro-chroman-4-ol derivatives were conveniently prepared through ruthenium-catalyzed asymmetric transfer hydrogenation using a dynamic kinetic resolution process. The reaction proceeded under mild conditions, affording the reduced fluorinated alcohols in good yields, high diastereomeric ratios, and excellent enantioselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Ting Chen, Wenjun Liu, Wei Gu, Shengtong Niu, Shouang Lan, Zhifei Zhao, Fan Gong, Jinggong Liu, Shuang Yang, Andrej Emanuel Cotman, Jinshuai Song, Xinqiang Fang
Summary: In this study, a unique dynamic kinetic resolution (DKR) mode was used to achieve the highly selective semi-transfer hydrogenation of unsymmetrical alpha-diketones. The distal carbonyl group was reduced while the proximal carbonyl remained untouched, resulting in the synthesis of enantioenriched acyclic ketones with alpha-hydroxy-alpha'-C(sp2)-functional groups. These products represent a new class of compounds that have not been previously reported. The utility of the synthesized compounds was demonstrated through further transformations, including the rapid synthesis of drug molecules. DFT calculations and control experiments were conducted to gain mechanistic insights into the highly selective semihydrogenation.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Baixue Liu, Peng Liu, Xue Wang, Feng Feng, Zhen Wang, Wenqiang Yang
Summary: A general method for the gram-scale enantioselective synthesis of P-stereogenic cyclic phosphine oxides has been developed using copper-catalyzed dynamic kinetic resolution, leading to high yields and high enantioselectivities. The resulting products can be easily reduced to obtain useful P(III)-stereogenic cyclic phosphines. A proposed mechanism involves the unusual rapid racemization of SPOs.
Article
Chemistry, Multidisciplinary
Muxing Zhou, Tatiana Gridneva, Zhenfeng Zhang, Ende He, Yangang Liu, Wanbin Zhang
Summary: This study presents an efficient route for the synthesis of chiral phthalidyl ester prodrugs using a chiral bicyclic imidazole organocatalyst and a continuous injection process. Computational studies suggest a general base catalytic mechanism different from the widely accepted nucleophilic catalytic mechanism. Analysis of key transition states reveals that CH-pi interactions, rather than previously considered cation/pi-pi interactions, play a dominant role in stereocontrol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Multidisciplinary Sciences
Tian-Jiao Han, Chun-Yan Guan, Na Li, Rui Dong, Li-Ping Xu, Xiao Xiao, Min-Can Wang, Guang-Jian Mei
Summary: A highly efficient dynamic kinetic resolution protocol for the atroposelective synthesis of heterobiaryls with vicinal C-C and N-N diaxes is reported. The combination of C-C biaryl with N-N nonbiaryl enables the synthesis of a novel class of vicinal-diaxis heterobiaryls.
Article
Chemistry, Organic
Artis Kinens, Simonas Balkaitis, Omar K. Ahmad, David W. Piotrowski, Edgars Suna
Summary: The study presents a non-enzymatic dynamic kinetic resolution (DKR) of secondary alcohols using an isothiourea-derived HyperBTM catalyst and Backvall's ruthenium complex, achieving high enantioselectivities at room temperature. A stereoinduction model based on cation-pi system interactions has been elaborated through DFT calculations.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Taichiro Touge, Hideki Nara, Michio Kida, Kazuhiko Matsumura, Yoshihito Kayaki
Summary: Efficient dynamic kinetic resolution of cyclic halohydrins was achieved by asymmetric transfer hydrogenation of racemic alpha-haloketones using bifunctional oxo-tethered Ru(II) catalysts. The catalyst could produce chiral alcohols with various functional groups with excellent diastereo- and enantioselectivities, providing a concise synthetic approach to a dopamine D3 receptor ligand, (+)-PHNO.
Article
Multidisciplinary Sciences
Kai Yang, Yanfei Mao, Zhihan Zhang, Jie Xu, Hao Wang, Yong He, Peiyuan Yu, Qiuling Song
Summary: The authors report a tetracoordinate boron-directed dynamic kinetic asymmetric transformation (DyKAT) method for the construction of C-B axial chirality using racemic, configurationally stable 3-bromo-2,1-azaborines. By rational design of a reversible tetracoordinate boron intermediate, a series of challenging C-B axially chiral compounds were prepared with generally good to excellent enantioselectivities. This method can also be extended to prepare atropisomers bearing adjacent C-B and C-C diaxes with excellent diastereo- and enantio-control.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Jamie S. Sweet, Ruichen Wang, Panagiotis Manesiotis, Paul Dingwall, Peter C. Knipe
Summary: The dynamic kinetic resolution of C-N atropisomeric pyridones was achieved via asymmetric phase-transfer catalysis, utilizing a hydrogen bond and pi interaction. The study revealed key non-covalent interactions between the substrate and catalyst.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Biki Ghosh, Reena Balhara, Garima Jindal, Santanu Mukherjee
Summary: The first catalytic enantioselective Fischer indolization of prochiral diketones containing enantiotopic carbonyl groups is developed through dynamic kinetic resolution. Catalyzed by a combination of a spirocyclic chiral phosphoric acid and ZnCl2, this approach efficiently synthesizes cyclopenta[b]indole derivatives with an all-carbon quaternary stereocenter in good to excellent enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Mariel M. Cardenas, Mirza A. Saputra, Deane A. Gordon, Andrea N. Sanchez, Nobuyuki Yamamoto, Jeffrey L. Gustafson
Summary: In this study, we reported the catalytic atroposelective syntheses of pharmaceutically relevant 3-arylquinolines through SNAr reactions mediated by Cinchona alkaloid-derived ureas. These reactions exhibited a range of dynamic kinetic resolution (DKR) and kinetic resolution (KR) characteristics, with different pathways depending on the stereochemical stability of the starting material. Furthermore, functionalization of the atropisomerically enriched quinolines into pharmaceutically privileged scaffolds was achieved with minimal observed racemization.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Hiroki Ishikawa, Taiga Yurino, Ryo Komatsu, Ming-Yuan Gao, Noriyoshi Arai, Taichiro Touge, Kazuhiko Matsumura, Takeshi Ohkuma
Summary: Racemic alpha-substituted alpha-amino esters were hydrogenated into enantioenriched beta-amino alcohols through dynamic kinetic resolution with chiral ruthenabicyclic complexes. The reaction proceeded with 1,2-hydride migration of the a-amino acetalate intermediate into the alpha-hydroxy imine followed by the continuous reduction of the imino compound, affording the amino alcohol product.
Article
Chemistry, Organic
Linghui Qian, Ling-Fei Tao, Wen-Tao Wang, Ehtesham Jameel, Zhang-Hong Luo, Tao Zhang, Yu Zhao, Jia-Yu Liao
Summary: An unprecedented atroposelective dynamic kinetic resolution of Bringmann's lactones with C-nucleophiles was reported. Activated isocyanides were used as the reagent to access novel axially chiral oxazole-substituted biaryl phenols in high yields with high enantioselectivities. The key to success lies in the tandem atroposelective addition of isocyanides to the lactone substrate followed by a rapid cyclization to overcome stereochemical leakage induced by lactol formation.
Article
Chemistry, Organic
Bin He, Jingyuan Song, Congcong Yin, Gen-Qiang Chen, Xumu Zhang
Summary: Asymmetric hydrogenation of aryldibenzylamino ketones catalyzed by the Ir/f-phamidol system was achieved through dynamic kinetic resolution, producing chiral compounds with high selectivity. This method offers excellent conversion and enantioselectivity, making it applicable in the synthesis of drug candidates and chiral ligands.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Multidisciplinary Sciences
Jianjian Liu, Mali Zhou, Rui Deng, Pengcheng Zheng, Yonggui Robin Chi
Summary: The authors report a synthetic method for the asymmetric synthesis of chiral sulfoxides using intramolecular chalcogen bonding interactions. The reaction involves conformational locking and facile isomerization enabled by chalcogen bonding interactions, leading to the formation of chiral sulfoxide products with excellent optical purities.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Martin Zahel, Yuzhou Wang, Anne Jaeger, Peter Metz
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Anton Kessberg, Peter Metz
Article
Chemistry, Organic
Yuzhou Wang, Peter Metz
Article
Chemistry, Organic
Anton Kessberg, Tilo Lueken, Peter Metz
Article
Chemistry, Organic
Julia Rautschek, Anne Jaeger, Peter Metz
Article
Chemistry, Organic
Yuzhou Wang, Ahmed F. Darweesh, Patrick Zimdars, Peter Metz
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Patrick Zimdars, Kristin Boehlig, Peter Metz
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Yuzhou Wang, Andre Hennig, Thomas Kuettler, Christian Hahn, Anne Jaeger, Peter Metz
Article
Multidisciplinary Sciences
Philipp Ciesielski, Peter Metz
NATURE COMMUNICATIONS
(2020)
Article
Chemistry, Organic
Felix Kaden, Peter Metz
Summary: In this study, the hydroazulene core of a bioactive sesquiterpenoid was generated by domino enediyne metathesis, with three out of four stereogenic centers of the target installed in a single step through a triple hydroboration/oxidation reaction. The enantiopure acyclic metathesis substrate was easily obtained via an asymmetric anti aldol reaction, and late-stage double carbonyl olefination was efficiently carried out after masking the gamma-lactone as an acetal.
Article
Chemistry, Multidisciplinary
Patrick Zimdars, Yuzhou Wang, Peter Metz
Summary: A concise and effective total synthesis of (-)-salvinorin A was achieved with high enantioselectivity and diastereoselectivity, using catalytic asymmetric propargylation and substrate-controlled reactions. The synthesis involved intramolecular Diels-Alder reactions and chemoselective Mitsunobu inversion, resulting in a streamlined reaction sequence with only 16 steps and 1.4% total yield. Additionally, an alternative strategy with a 2-bromo-1,3-diene moiety was explored.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Felix Kaden, Susanne Nowotni, Franziska Hoefner, Melanie Lorenz, Andre Barthel, Anne Jaeger, Felix Hennersdorf, Jan J. Weigand, Peter Metz
Summary: An efficient total synthesis of (-)-dehydrocostus lactone was achieved through a multi-step approach involving stereoselective reactions, hydroboration/oxidation, and olefination, significantly improving the efficiency of the synthesis process.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
