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, 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, 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
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, 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
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
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
Zhaofeng Gao, Jingwen Liu, Haizhou Huang, Huiling Geng, Mingxin Chang
Summary: The research reports on efforts to merge two asymmetric reductive amination reactions into a single-step transformation, utilizing specific catalyst and acid additives to successfully synthesize enantiopure secondary amine products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Wang Rui-Xiang, Zhao Qing-Ru, Gu Qing, You Shu-Li
Summary: In this study, gold- and iridium-catalyzed alkynylamide cyclization/asymmetric allylic benzylation cascade reactions were developed. Enantioenriched oxazole derivatives with a benzylic stereogenic center were obtained in good yields and high enantioselectivities. The general procedure involves the preparation of a chiral iridium complex solution, followed by the addition of reactants and catalyst. The reaction mixture is stirred at 40 degrees C until completion and the product is purified.
ACTA CHIMICA SINICA
(2023)
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, Multidisciplinary
Qing-Ru Zhao, Ru Jiang, Shu-Li You
Summary: An efficient strategy was developed to access a series of axially chiral styrenes by iridium-catalyzed allylic substitution and central-to-axial chirality transfer via olefin isomerization. The method provides a broad range of axially chiral styrenes with moderate to excellent yields and enantioselectivity, offering a powerful tool in asymmetric organic synthesis.
ACTA CHIMICA SINICA
(2021)
Review
Chemistry, Multidisciplinary
Yaru Gao, Guorong Hong, Bin-Miao Yang, Yu Zhao
Summary: Direct substitution of readily available alcohols is an important area of research in green chemical synthesis. Catalytic enantioconvergent transformations of racemic secondary alcohols are desired for efficient access to valuable enantiopure compounds. The enantioconvergent borrowing hydrogen methodology has proven to be effective for achieving such transformations. This review provides an overview of the progress made in the past decade, focusing on the conversion of racemic secondary alcohols to enantioenriched chiral amines, N-heterocycles, higher-order alcohols, and ketones.
CHEMICAL SOCIETY REVIEWS
(2023)
Review
Chemistry, Multidisciplinary
Xi Wang, Youbin Peng, Ling Zhao, Xiaohong Huo, Wanbin Zhang
Summary: Compared to the stereocontrol of the stereocenter at the allyl unit, asymmetric induction of prochiral nucleophiles is a challenging task in Pd-catalyzed asymmetric allylic substitutions due to the remote distance between the chiral catalyst and the prochiral nucleophile. Extensive efforts have been made to address this challenge through the design of chiral ligands. Recently, synergistic catalysis, including bimetallic catalysis and Pd/organocatalysis, has gained attention for its potential advantages in improving reactivity and selectivity, and providing a simple and unified method for the stereocontrol of prochiral nucleophiles. This review summarizes the history and advances in this field.
SCIENCE CHINA-CHEMISTRY
(2023)
