Article
Chemistry, Organic
Meng-Lan Shen, Pu-Sheng Wang, Liu-Zhu Gong
Summary: A regioselective Pd-catalyzed allylic amination reaction has been developed, which can generate either branched Z-dienyl allylic amines or linear conjugated allylic amines with high levels of regioselectivity from the same substrates by tuning the reaction conditions.
Article
Chemistry, Organic
Chao Xia, Dong-Chao Wang, Gui-Rong Qu, Hai-Ming Guo
Summary: A highly enantioselective allylation reaction of vinylethylene carbonate by asymmetric palladium catalysis has been developed for various N-heteroaromatic substrates. The efficient synthesis of acyclic nucleoside analogs with high yields (up to 96%) and enantioselectivities (up to 99%) was demonstrated with only 0.5 mol% of Pd catalyst. Additionally, these acyclic nucleosides can undergo rapid transformation into a variety of structurally diverse chiral acyclic nucleosides and isonucleosides.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Chemistry, Organic
Rajan Archana, Thaipparambil Aneeja, Gopinathan Anilkumar
Summary: This review provides an overview of the research progress in ruthenium-catalyzed allylic amination reactions, including a summary and analysis of the literature up to 2021.
CURRENT ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Juping Wang, Rongxing Xiao, Kangcheng Zheng, Li Qian
Summary: This study investigated the mechanism and selectivity of Mn-catalyzed intermolecular C-H amination of internal olefin using B3LYP functional. It was found that the regioselectivity of the reaction can be enhanced by introducing a bulky, strong electron-withdrawing group on the substrate.
MOLECULAR CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
T. Parker Maloney, Alexander F. Dohoda, Alec C. Zhu, Forrest E. Michael
Summary: In this study, we reported a convenient and transition metal-free intermolecular propargylic C-H amination of alkynes. The reaction showed high yields for terminal, silyl, and internal alkynes with a wide range of functional groups. The regioselectivity of amination was found to be influenced by substitution pattern and relatively remote heteroatomic substituents.
Article
Chemistry, Organic
Ze-Liang He, Peng Chen, Zhi-Chao Chen, Wei Du, Ying-Chun Chen
Summary: A cascade assembly method for synthesizing 1,2,3,4-tetrahydrodibenzo[b,d]-furan architectures incorporating a spirooxindole motif has been developed with moderate to good yields and excellent diastereoselectivity. Fused indole analogues can similarly be obtained by employing benzylideneacetones with an o-TsNH group.
Article
Chemistry, Organic
Yinan Ai, Hanlin Yang, Chunying Duan, Xingwei Li, Songjie Yu
Summary: A new Co-catalyzed sequential C-C and C-F activation of gem-difluorinated cyclopropanes has been developed, allowing the formation of nucleophilic fluoroallylcobalt, followed by addition to aldehydes to yield linear (Z)- and (E)-fluorinated homoallylic alcohols. This discovery established a new strategy for the efficient transformation of gem-difluorinated cyclopropanes and synthesis of challenging fluorinated homoallylic alcohols.
Article
Chemistry, Organic
Xiaoying Li, Peihe Li, Zheng Wang, Hui Fu, Qipu Dai
Summary: Allylamine compounds were synthesized in one step by using aroyloxycarbamates as starting material, which was prepared in situ by inexpensive carboxylic acid and hydroxylamine. The reaction conditions are mild and the substrate is generally applicable, and it also achieved the synthesis of indole.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Nuria Vazquez-Galinanes, Isabel Velo-Heleno, Martin Fananas-Mastral
Summary: A method for the use of vinyl epoxides in catalytic allylboration of alkynes is described, which allows for the synthesis of bifunctional skipped dienes bearing both an allylic alcohol and an alkenylboronate from simple starting materials with high regio- and stereoselectivity. These products show versatile reactivity and can be converted into cyclic boron compounds and polyenes.
Article
Chemistry, Multidisciplinary
Rui-Han Dai, Lu Han, Qi Wang, Shi-Kai Tian
Summary: A new strategy has been established for the [2,3]-sigmatropic rearrangement of quaternary allylammonium ylides, delivering structurally diverse N-cyclobutyl homoallylamines in moderate to excellent yields. This method provides a new approach for the synthesis of allylamine compounds.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Tingting Cao, Pascal Retailleau, Thierry Milcent, Benoit Crousse
Summary: We report the synthesis of a novel family of N-CF3 hydrazines using the available and cheap Langlois reagent. These derivatives exhibit very high stability under different conditions and are excellent precursors for building previously inaccessible N-CF3 functionalized compounds.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Pu-Sheng Wang, Liu-Zhu Gong
Summary: Pd-catalyzed asymmetric allylic C-H functionalization is a powerful tool to access chiral and densely functionalized molecules from easily accessible alkenes, resulting in increased step- or atom-economy by minimizing functional group manipulations. However, due to inadequate stereoselection strategies, this field is still in its early stage. This essay describes the journey to identify asymmetric catalytic systems, the mechanism of allylic C-H activation, control of stereo- and regioselectivity, and applications in asymmetric synthesis.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Xiangbin Bai, Linlin Qian, Hong-Hao Zhang, Shouyun Yu
Summary: This study presents an enantioselective radical alkylation of 4-alkyl-1,4-dihydropyridines with Morita-Baylis-Hillman (MBH) adducts using dual photoredox/palladium catalysis, yielding products with good yields and enantioselectivity. The use of Ding's spiroketal-based bis-(phosphine) (SKP) ligand is crucial for achieving satisfactory regio- and enantioselectivity in this reaction. The resulting alpha,beta-unsaturated ester can be easily reduced to a synthetically useful chiral allyl alcohol.
Article
Chemistry, Multidisciplinary
Ling-Qi Chen, Chi-Fan Zhu, Su Zhang, Bao-Yang Liu, Shu-Jiang Tu, Wen-Juan Hao, Bo Jiang
Summary: A new palladium-catalyzed annulative allylic alkylation reaction has been developed for the regioselective synthesis of tetracyclic cyclic ethers with bridged aryl-indole scaffolds.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Organic
Jia-Le Zheng, Fei Liu, Xue Song, Zhi Zhao, Wei Du, Ying-Chun Chen
Summary: In this study, we found that dienones generated from the Morita-Baylis-Hillman carbonates of 2-cyclopentenone under Pd(0) catalysis could be umpolunged through pi-Lewis base activation to form regioselective eta 2-Pd(0) complexes, which then underwent asymmetric inverse-electron-demand oxa-Diels-Alder reaction with alpha-cyano chalcones. This study successfully constructed a range of fused pyran frameworks with dense substitutions and demonstrated excellent stereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
