Article
Chemistry, Organic
Zhifang Chen, Yufeng Zhou, Tingjun Hu, Heng-Ying Xiong, Guangwu Zhang
Summary: This unprecedented 1,3-dipole cycloaddition between acyclic CF3-ketimines and N-benzyl azomethine ylide has been enabled by tungsten catalysis, leading to a range of novel imidazolidines with a trifluoromethylated tetrasubstituted carbon center. The gram-scale synthesis capability and variant derivatizations of cycloaddition adducts demonstrate the synthetic potential of this approach, providing easy access to a rapidly expanding library of motifs with a trifluoromethylated fully substituted carbon.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Anand Pariyar, Debesh Sharma, Sagarmani Rasaily, Shivanand Chettri, Disha Sureka, Sudarsan Tamang
Summary: This study reports the synthesis of a novel 2D metal-organic framework with pre-existing unsaturated Lewis acid sites, which can be directly used for catalyzing organic transformations and synthesizing biologically active chiral imidazolidines. The material exhibits excellent reusability and high stereoselectivity.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jing Zhang, Yi-Fei Li, Feng-Cheng Jia, Yang Gao, Xiao-Qiang Hu
Summary: This study successfully achieves the first [3 + 2] annulation of readily available 3-aminooxetanes and 1,3,5-triazinanes. The reaction conditions are mild and operation is simple, leading to the synthesis of a range of structurally diverse 4-hydroxymethyl imidazolidines.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Shohei Furuya, Kenji Muroi, Kazuya Kanemoto, Shin-ichi Fukuzawa
Summary: The stereodivergent asymmetric synthesis of 2,5-trans/cis pyrrolidines by 1,3-dipolar cycloaddition using two different types of activated alkenes is described. The reaction using ylidene-isoxazolones as dipolarophiles produced 2,5-trans pyrrolidines, while the reaction using acyclic enones as activated alkenes afforded 2,5-cis substituted pyrrolidines.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Arthur Lebrene, Thomas Martzel, Laura Gouriou, Morgane Sanselme, Vincent Levacher, Sylvain Oudeyer, Carlos Afonso, Corinne Loutelier-Bourhis, Jean-Francois Briere
Summary: A straightforward method for synthesizing original 1,6-diazabicyclo[4.3.0]nonane-2,7-diones was developed using a DBU-organocatalyzed multicomponent Knoevenagel-aza-Michael-Cyclocondensation reaction. Analysis of key reactive intermediates using mass spectrometry confirmed the proposed mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Zhigang Chen, Wei Zhong, Sihua Liu, Ting Zou, Kaiqiang Zhang, Chuliang Gong, Wenyan Guo, Feizhi Kong, Libo Nie, Shunqin Hu, Haifei Wang
Summary: In this study, we report the highly diastereo- and enantioselective [3 + 2] cycloadditions of iminoesters with various alpha-substituted acrylates. The reactions are catalyzed by AgHMDS/DTBM-Segphos or Ag2O/CA-AA-Amidphos, and result in the stereodivergent synthesis of chiral C4-ester-quaternary exo- or endo-pyrrolidines with high yields and excellent diastereo- and enantioselectivities (up to >99:1 dr and >99% ee). The gram-scale synthetic exo-adduct is particularly significant, as it enables the total synthesis of the spirotryprostatin A alkaloid in nine steps with a 36% overall yield.
Article
Chemistry, Multidisciplinary
Houda Gazzeh, Fadwa Rouatbi, Sami Chniti, Moheddine Askri, Michael Knorr, Carsten Strohmann, Christopher Golz, Al Mokhtar Lamsabhi
Summary: The mechanism of a three-component one-pot cycloaddition reaction was studied using both theoretical and experimental methods. The reactivity difference between the unsymmetrical exocyclic dienones was analyzed to explain the observed regio- and stereoselectivity, and the results were confirmed by calculations. The reaction proceeded under kinetic control and showed chemoselectivity, producing two highly diastereomerically enriched compounds. The intermolecular hydrogen bonding and optical properties of the products were also investigated.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Mamta Gill, Arko Das, Vinod K. Singh
Summary: An enantioselective (3+2) cycloaddition reaction has been reported for the synthesis of chiral polysubstituted pyrrolidines. The reaction displays opposite regioselectivity with excellent enantioselectivities and yields. Interestingly, changing the alpha-substituents of the iminoesters results in the formation of normal (3+2) cycloaddition products with excellent enantioselectivities as well.
Article
Chemistry, Organic
Jose Cortes Vazquez, Jacqkis Davis, Vladimir N. Nesterov, Hong Wang, Weiwei Luo
Summary: A formal [3 + 3] cyclization reaction has been developed for the synthesis of 1,3,4-oxadiazinanes with generally high yields (up to 96%). The reaction, catalyzed by Sc(OTf)(3), has a broad substrate scope for both diaziridines and quinones. The synergistic activation of 1,3-dipolar diaziridines and dipolar quinones was found to be essential for enabling this reaction.
Article
Chemistry, Applied
Kai-Kai Wang, Yan-Li Li, Rong-Xiang Chen, Ai-Li Sun, Zhan-Yong Wang, Ying-Chao Zhao, Ming-Yue Wang, Shi Sheng
Summary: The additive-free 1,3-dipolar cycloaddition reaction enables diversity-oriented synthesis of novel and structurally complex derivatives in high yields and excellent diastereoselectivities.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Biochemistry & Molecular Biology
Guipeng Feng, Guoyang Ma, Wenyan Chen, Shaohong Xu, Kaikai Wang, Shaoyan Wang
Summary: The [3 + 2] 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines with allyl alkyl ketones has been achieved, resulting in a range of tetrahydroisoquinoline derivatives with good diastereoselectivities and enantioselectivities. The absolute configuration of the product was determined using quantum electronic circular dichroism calculation and ECD spectrum method.
Article
Chemistry, Applied
Jing Huang, Bo Jiang, Xiyuan Zhang, Yanfeng Gao, Xiufang Xu, Zhiwei Miao
Summary: A synthetic strategy for accessing functionalized azabicyclo[3.3.1]alkenones with three tertiary stereocenters has been developed. The method is scalable and the products can be transformed to various eight-membered-ring bridged heterocyclic molecules.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Lei Zhang, Wei Quan, Ren-Ming Liu, You-Ping Tian, Bo-Wen Pan, Xiong-Li Liu
Summary: A highly efficient strategy for the diverse synthesis of structural bispiro[butyrolactone-pyrrolidine-indanedione] hybrids is achieved for the first time using 1,3-dipolar cycloadditions. The strategy involves the reaction between α,β-unsaturated butyrolactones/valerolactones and azomethine ylides, which are generated in situ from ninhydrin and proline or thioproline. The target compounds, with potential bioactivity, are obtained in good yields and diastereoselectivities.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Silvia Vera, Ana Vazquez, Ricardo Rodriguez, Sandra Del Pozo, Inaki Urruzuno, Abel de Cozar, Antonia Mielgo, Claudio Palomo
Summary: This study reports a highly enantio- and syn-selective synthesis of beta-hydroxy alpha-amino acids from glycine imine derivatives under Bronsted base catalysis. The key lies in the use of benzophenone-derived imine of glycine o-nitroanilide as a pronucleophile, where the o-nitroanilide framework provides an efficient hydrogen-bonding platform that accounts for nucleophile reactivity and diastereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yabo Deng, Zhenghao Dong, Fengyun Gao, Yifei Guo, Mengmeng Sun, Yongzhen Li, Yalan Wang, Qushuo Chen, Kairong Wang, Wenjin Yan
Summary: An amino-controlled regiodivergent asymmetric synthesis of CF3-containing spiro-pyrrolidine-pyrazolone compounds is described, offering adducts in excellent yields, dr, and ee when using alkaloid-derived squaramide as the catalyst. Switching to cyclohexanediamine-derived squaramide led to the formation of a series of structural isomers through a switched umpolung reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
