Article
Chemistry, Applied
Xiaoding Jiang, Bendu Pan, Xu Qian, Hao Liang, Yaqi Zhang, Bin Chen, Xiaobo He, Hoi Shan Chan, Albert S. C. Chan, Liqin Qiu
Summary: In this study, the iridium-catalysed enantioselective intramolecular allylic substitution of pyrimidine-tethered allylic carbonates was developed, leading to the successful construction of a wide range of chiral pyrimidine-fused diazepinone derivatives with high yields and enantiomeric excesses. This work further highlights the power of chiral-bridged biphenyl phosphoramidites in asymmetric synthesis.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Zeng-Hua Wu, Huai-Yu Wang, Huai-Lan Yang, Li-Hua Wei, Tamio Hayashi, Wei-Liang Duan
Summary: An iridium-catalyzed asymmetric synthesis of branched allylic phosphine compounds with excellent stereoselectivity and regioselectivity is reported. The use of phosphine sulfides with low deactivation capacity is crucial for the success of this reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Xin Yu, Lingfei Hu, Wolfgang Frey, Gang Lu, Rene Peters
Summary: Catalytic allylic substitution is an important method in asymmetric synthesis to generate C-C bonds with enantioselectivity. However, a common limitation is the formation of allylic substitution products with (E)-configured C=C double bonds. In this study, a planar chiral palladacycle catalyst was used to achieve a diastereospecific reaction outcome, maintaining the C=C double bond geometry of the allylic substrates in highly enantioenriched products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Pusu Yang, Rui-Xiang Wang, Yuan-Zheng Cheng, Chao Zheng, Shu-Li You
Summary: This study describes an iridium-catalyzed asymmetric allylic benzylation reaction under light irradiation. 2-methylbenzophenone derivatives were activated by ultraviolet light, enabling high enantioselectivity without the use of strong bases or pre-activation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Xiaohong Huo, Guanlin Li, Xi Wang, Wanbin Zhang
Summary: Bimetallic catalysis is an efficient strategy for developing new chemical reactions and stereodivergent synthesis, allowing for the preparation of products with different stereoisomers from the same set of starting materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Qi Zhang, Si-Wei Zhou, Chang-Yun Shi, Liang Yin
Summary: A catalytic asymmetric allylic substitution using copper(I) homoenolates as nucleophiles has been achieved, with high yields and enantioselectivity. The method is applicable to a broad range of substrates and can be extended to the construction of chiral quaternary carbon centers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Madhawee K. Arachchi, Hien M. Nguyen
Summary: A broadly applicable methodology has been developed for the regio- and enantioselective construction of branched allylic carbon-heteroatom bonds from racemic, secondary allylic trichloroacetimidates. The products containing allylic C-O, C-N, and C-S bonds are obtained in synthetically useful yield and selectivity. Additionally, the chiral diene-ligated iridium catalyst is effective at promoting asymmetric aminations of acyclic secondary anilines.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Wei Zhao, Wenji Wang, Huan Zhou, Qishan Liu, Zhiqing Ma, Haizhou Huang, Mingxin Chang
Summary: A one-pot asymmetric hydrogenation of pyridines with subsequent N-alkylation using a traceless Bronsted acid activation strategy is reported. The reaction exhibits high stereoselectivity and can be used to synthesize indolizidines and quinolizidines. Experimental and theoretical studies reveal that chloride anion and noncovalent interactions play important roles in determining the stereoselectivity of the reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Jiamin Lu, Meifang Wang, Ruigang Xu, Haizhou Sun, Xuan Zheng, Guofu Zhong, Xiaofei Zeng
Summary: The highly efficient direct asymmetric allylic substitution (AAS) reaction of indolizine derivatives with allylic alcohols was achieved by combining a chiral iridium complex catalyst with Lewis acid under mild conditions, delivering enantioenriched products in high yields and excellent selectivities. This protocol stands out for its availability of starting materials, mild conditions, broad substrate scope, high yields, excellent selectivity, and easy scalability, providing an efficient approach for the synthesis of chiral indolizines.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Hang-Fei Tu, Yu-Han Nie, Chao Zheng, Shu-Li You
Summary: We report a catalytic synthetic method for enantioenriched N-substituted pyridones in this study. By using a chiral iridium catalyst generated from the Carreira [P/olefin] ligand, intermolecular asymmetric allylic amination between allyl alcohols and pyridones proceeded smoothly with excellent chemo-, regio-, and enantioselectivities. This method displayed a broad substrate scope for both pyridones and allylic alcohols and showed potential for diverse transformations of the amination products to useful skeletons.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Jia-Hao Xie, Yi-Ming Hou, Zuolijun Feng, Shu-Li You
Summary: Here, we describe a synthesis method for cyclohexanones with multiple continuous stereocenters by combining copper-catalyzed asymmetric conjugate addition of dialkylzinc reagents to cyclic enones with iridium-catalyzed asymmetric allylic substitution reaction. The reaction yields good to excellent results in terms of yield, diastereoselectivity, and enantioselectivity. Unlike previous studies focusing on adjacent stereocenter construction (1,2-position), this reaction achieves stereodivergent construction of nonadjacent stereocenters (1,3-position) by utilizing two chiral catalysts with different enantiomers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Xi-Jia Liu, Wen-Yun Zhang, Chao Zheng, Shu-Li You
Summary: Herein, an Ir-catalyzed asymmetric allylic substitution reaction of methyl azaarenes is reported. The reaction exhibits high yields and enantioselectivity, and utilizes the Knochel reagent for the formation of benzylic nucleophiles without additional activating reagents. The synthetic utility of this method has been demonstrated by an enantioselective synthesis of an allosteric protein kinase modulator.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Bing-Ke Zhu, Hui Xu, Lu Xiao, Xin Chang, Liang Wei, Huailong Teng, Yanfeng Dang, Xiu-Qin Dong, Chun-Jiang Wang
Summary: Highly diastereo-/enantioselective assembly of 2,3-fused indolizine derivatives could be achieved through a cascade allylation/Friedel-Crafts type reaction enabled by a synergistic Cu/Ir catalysis. This method provides a facile route to enantioenriched indolizines with three stereogenic centers, showing excellent stereoselective control and broad substrate generality. The synthetic utility of this method was demonstrated by gram-scale reactions and transformations to other important chiral indolizine derivatives.
Article
Chemistry, Multidisciplinary
Min Liu, Haiying Zhao, Changkun Li
Summary: A highly regio- and enantioselective allylic alkylation of Meldrum acid with racemic allylic substrates bearing alkyl groups has been developed using a Rh(I) catalyst. The use of a chiral bisoxazopinephosphine ligand is essential for high yields and selectivities, providing rapid access to various chiral beta-alkyl-gamma,delta-unsaturated carboxylic acids and their derivatives.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Physical
Shengtong Niu, Yingkun Luo, Chao Xu, Jinggong Liu, Shuang Yang, Xinqiang Fang
Summary: In this work, a general protocol for copper-catalyzed allylic substitutions using stable soft nucleophiles has been developed, resulting in the synthesis of highly selective functionalized 1,3- and 1,4-enynes. Mechanistic studies propose a copper acetylide-bonded allylic cation as the key intermediate, featuring an outer-sphere nucleophilic attack. The demonstrated diversified reactivities in this study will inspire further exploration.
Article
Chemistry, Multidisciplinary
Ata Makarem, Regina Berg, Frank Rominger, Bernd F. Straub
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Article
Chemistry, Multidisciplinary
Matthias W. Hussong, Wilhelm T. Hoffmeister, Frank Rominger, Bernd F. Straub
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Article
Chemistry, Organic
Anne L. Schoeffler, Ata Makarem, Frank Rominger, Bernd F. Straub
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Editorial Material
Chemistry, Organic
Bernd F. Straub, Rolf Gleiter, Claudia Meier, Lutz H. Gade
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Multidisciplinary
Matthias W. Hussong, Frank Rominger, Petra Kraemer, Bernd F. Straub
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2014)
Review
Chemistry, Organic
Regina Berg, Bernd F. Straub
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2013)
Article
Chemistry, Physical
Simone G. Weber, David Zahner, Frank Rominger, Bernd F. Straub
Article
Chemistry, Multidisciplinary
T. Sohner, F. Braun, L. C. Over, S. Mehlhose, F. Rominger, B. F. Straub
Article
Chemistry, Organic
Claudine Schlemmer, Lars Andernach, Dieter Schollmeyer, Bernd F. Straub, Till Opatz
JOURNAL OF ORGANIC CHEMISTRY
(2012)
Article
Chemistry, Inorganic & Nuclear
Stefanie C. Holm, Frank Rominger, Bernd F. Straub
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2012)
Article
Chemistry, Inorganic & Nuclear
Stefanie C. Seitz, Frank Rominger, Bernd F. Straub
Article
Chemistry, Multidisciplinary
Oliver Trapp, Saskia Lamour, Frank Maier, Alexander F. Siegle, Kerstin Zawatzky, Bernd F. Straub
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Organic
Timo Soehner, Ina K. Kueppers, Wiebke Wackerow, Frank Rominger, Bernd F. Straub
Article
Chemistry, Multidisciplinary
Florian Beuerle, Anke Krueger, Matthias Lehmann, Thorsten Bach, Uwe Beifuss, Thomas J. J. Mueller, Ralf Giernoth, Klaus Ditrich, Bernd F. Straub, Peter R. Schreiner, Thomas Lindel, Dietrich Boese, Joerg Pietruszka, Roland Pfau, Rolf Breinbauer, Norbert Sewald, Elmar Weinhold, Christoph Arenz, Jennifer Andexer, Michael Mueller, Wolfgang von Deyn, Markus Kordes, Christine Wiebe, Kilian Muniz, Stefan Braese, Mathias O. Senge, Jan Paradies, Burkhard Luy, Claudia Muhle-Goll, Moritz Bosse Biskup
NACHRICHTEN AUS DER CHEMIE
(2013)
Article
Chemistry, Multidisciplinary
Florian Beuerle, Anke Krueger, Matthias Lehmann, Thorsten Bach, Uwe Beifuss, Thomas J. J. Mueller, Mathias O. Senge, Ralf Giernoth, Klaus Ditrich, Jan Paradies, Kilian Muniz, Bernd F. Straub, Peter R. Schreiner, Detlef Schroeder, Thomas Lindel, Joerg Pietruszka, Christoph Soeffing, Roland Pfau, Rolf Breinbauer, Norbert Sewald, Elmar Weinhold, Moritz Bosse Biskup, Gerald Draeger, Christoph Arenz, Jennifer Andexer, Michael Mueller, Wolfgang von Deyn, Trevor Newton, Joachim Rheinheimer, Claudia Muhle-Goll, Burkhard Luy, Stefan Braese
NACHRICHTEN AUS DER CHEMIE
(2012)