Article
Chemistry, Organic
Laxman Devidas Khalse, Sachin S. Gorad, Prasanta Ghorai
Summary: In this study, a new Cu(II)-(S,S)-Pr-i-FOXAP catalyst was reported for the borylative Michael/Michael addition cascade cyclization of unsymmetrical dienone, leading to the synthesis of highly substituted and functionalized spiroindane boronates under mild conditions. A series of optically active spiroids bearing boronic ester were obtained with excellent yields and good to excellent enantioselectivities and diastereoselectivities.
Article
Chemistry, Organic
Xiaosa Lu, Jie Zhu, Yinhua Huang
Summary: A rhodium-catalyzed highly enantio- and diaster-eoselective alkenylation reaction of Ay-unsaturated butenolides is reported. The use of a chiral diene ligand enables the synthesis of chiral butyrolactones in high yields with extremely high enantioselectivities and high diastereoselectivities. The key process involves the isomerization of butenolides and subsequent dynamic kinetic resolution.
Article
Chemistry, Organic
Fang Xie, Jie Zhao, Deyue Ren, Jianming Xue, Jingyi Wang, Qin Zhao, Lu Liu, Xiaodan Liu
Summary: A Cu-catalyzed coupling reaction between cyclic imino esters and 2H-azirines has been developed, allowing for the synthesis of novel optically active aziridines in high yields and with excellent levels of diastereo- and enantioselectivities under mild conditions. This method features a broad substrate scope, good functional group compatibility, and enriches the existing reaction type for the rapid synthesis of optically active aziridines bearing vicinal tetrasubstituted stereogenic carbon centers.
Article
Chemistry, Organic
Hyun Ji Jeon, Su Min Park, Yu Lim Lee, Sang-gi Lee
Summary: The palladium-catalyzed divergent asymmetric synthesis of chiral spiro-furanindoline derivatives is described. The zwitterionic alkoxy pi-allyl Pd(II) intermediate, generated catalytically from vinyl ethylene carbonate (VEC), could undergo ligand-controlled enantio-and diastereoselective dipolar [3 + 2] spiroannulation with indole-based azadienes to afford the optically active spiro-furanindolines embedding an all-carbon quaternary stereocenter in high yields (up to 99%) with good to excellent stereoselectivities (up to 99% ee and up to >94:6 dr).
Article
Chemistry, Multidisciplinary
Andrea Chaves-Pouso, Andres M. Alvarez-Constantino, Martin Fananas-Mastral
Summary: Allylic gem-dichlorides can be efficient substrates for catalytic asymmetric allylboration of alkynes. The method generates chiral skipped dienes with excellent levels of chemo-, regio- enantio- and diastereoselectivity, making them versatile building blocks for the synthesis of optically active compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Yoshikazu Horino, Mayo Ishibashi, Juri Sakamoto, Miki Murakami, Toshinobu Korenaga
Summary: The diastereoselective synthesis of anti-homoallylic alcohols bearing conjugated (Z)-enynes through a palladium-catalyzed three-component reaction is described, featuring a broad substrate scope, good functional group compatibility, and high levels of (Z)-alkene stereocontrol. The reaction involves Pd(0) functioning as a catalyst in two fundamental steps: the generation of a borylated pi-allylpalladium species inducing umpolung allylation of aldehydes, and C(sp(2))-C(sp) cross-coupling. Further transformations of the obtained products highlight their synthetic utility.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Andrea Chaves-Pouso, Andres M. Alvarez-Constantino, Martin Fananas-Mastral
Summary: In this Communication, Martin Fananas-Mastral et al. report an enantio- and diastereoselective copper-catalyzed allylboration of alkynes with allylic gem-dichlorides.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Hiroto Uno, Koki Kawai, Taichi Araki, Motoo Shiro, Norio Shibata
Summary: Gem-difluoromethylene moieties are attractive in medicinal chemistry due to their ability to mimic other more ubiquitous functional groups. A novel asymmetric method for their construction was developed, allowing easy access to chiral 1,3-dioxanes that contain a tetrasubstituted difluoroalkyl stereogenic center. The gem-difluoro substitution pattern promotes the reaction, and various substrates were suitable for this method.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Jun-Hao Zhang, Hui Xu, Xiaodong Tang, Yanfeng Dang, Fa-Guang Zhang, Jun-An Ma
Summary: In this study, the efficient and stereoselective hydrogenation of congested tetra-substituted cyclic beta-enamido phosphonates/phosphine oxides was achieved using a commercially available Rh-Josiphos system. This method enables the synthesis of chiral beta-amino phosphorus compounds with two vicinal stereocenters. The protocol is applicable to various ring systems and different phosphonate/phosphine oxide groups, and it has been successfully applied to the preparation of amino-phosphine ligands. The DFT mechanistic explorations suggest that the C=C migratory insertion into the Rh-III-H bond is the rate- and stereo-determining step, and the origins of stereoselectivity are regulated by dispersion interactions and steric repulsions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Minami Otsubo, Kousuke Sakimoto, Hiromichi Egami, Yoshitaka Hamashima
Summary: In this study, enantio- and diastereoselective fluorination of naphthoresorcinol and resorcinol derivatives was achieved for the first time using a dicarboxylate phase-transfer catalyst. The chiral catalyst showed good efficiency and selectivity in the reactions, providing difluorination products preferentially.
Article
Chemistry, Multidisciplinary
Chao Che, Yi-Nan Lu, Chun-Jiang Wang
Summary: A novel strategy for catalytic asymmetric synthesis of enantioenriched 3-cis- and 3-trans-substituted prolines has been successfully developed via a unique cascade radical addition/cyclization enabled by synergistic photoredox/Bronsted acid catalysis and subsequent base-assisted epimerization. This method provides a de novo access to all four stereoisomers of 3-substituted prolines, which cannot be readily obtained using current established methods. The methodology can also be extended to the asymmetric synthesis of the full complement of stereoisomers of 3-substituted pipecolinic acids.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Jian Chen, Lifu Wu, Yue Zhao, Shaolin Zhu
Summary: In this study, we report a catalytic reaction that can control two stereocenters simultaneously. By using a chiral catalyst, we achieved simultaneous control of the stereocenters in two substrates, resulting in the formation of high-value products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Chiara Portolani, Giovanni Centonze, Sara Luciani, Andrea Pellegrini, Paolo Righi, Andrea Mazzanti, Alessia Ciogli, Andrea Sorato, Giorgio Bencivenni
Summary: The first catalytic enantioselective and diastereoselective synthesis of atropisomeric hydrazides was achieved using a sequential catalysis protocol, providing a stereodivergent approach to enantioenriched atropisomeric hydrazides. The resulting axially chiral hydrazides were obtained directly from commercially available reagents in high yields and with good stereocontrol, demonstrating the effectiveness of this strategy.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Sheng Zuo, Yuan Tao, Zhigang Liu, Ke Zhang, Luyun Zhang, Yingtang Ning, Fen-Er Chen
Summary: This study successfully synthesized highly congested indanone-based spirolactones through copper-catalyzed decarboxylative propargylation, with the key role of DPEN-based ligands. The method tolerated a wide range of functional groups, yielding high diastereo- and enantioselectivities. Mechanistic observations indicated the capability of the new copper complex to enable stereocontrolled addition to copper-allenylidene species.
Article
Chemistry, Multidisciplinary
Sabrina Giofre, Letizia Molteni, Donatella Nava, Leonardo Lo Presti, Egle Maria Beccalli
Summary: Excellent enantio- and diastereoselectivity can be achieved in the oxidative Pd-catalyzed dioxygenation of (aza-)alkenols by using specific chiral ligands and hypervalent-iodine compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
James D. Vasta, Amit Choudhary, Katrina H. Jensen, Nicholas A. McGrath, Ronald T. Raines
Article
Chemistry, Organic
Katrina H. Jensen, Matthew S. Sigman
JOURNAL OF ORGANIC CHEMISTRY
(2010)
Article
Chemistry, Multidisciplinary
Katrina H. Jensen, Tejas P. Pathak, Yang Zhang, Matthew S. Sigman
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2009)
Article
Chemistry, Multidisciplinary
Katrina H. Jensen, Jonathan D. Webb, Matthew S. Sigman
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2010)
Review
Chemistry, Analytical
Katrina H. Jensen, Brian W. Michel
Summary: This article discusses the importance and challenges of ethylene detection, introduces two main approaches based on coordination and activity, and discusses the advantages and disadvantages of various methods.
ANALYSIS & SENSING
(2023)
Article
Chemistry, Multidisciplinary
Katrina H. Jensen, Matthew S. Sigman
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2007)