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, 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, Multidisciplinary
Guangjun Bao, Peng Wang, Guofeng Li, Changjun Yu, Yiping Li, Yuyang Liu, Zeyuan He, Tiantian Zhao, Jing Rao, Junqiu Xie, Liang Hong, Wangsheng Sun, Rui Wang
Summary: A new method for 1,3-dipolar cycloaddition reactions between different types of amino acids to generate various quaternary amino acids was disclosed in this study. This method can also be applied within peptide chains, providing a new approach for late-stage peptide modification and drug conjugation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Linlong Dai, Qiaohong Zhu, Jie Zeng, Yuheng Liu, Guofu Zhong, Xiaoyu Han, Xiaofei Zeng
Summary: The study presents an effective strategy for the synthesis of chiral imidazolidines through catalytic reactions, achieving high yields and enantioselectivities. Additionally, this method can also be applied in the synthesis of chiral vicinal diamines by adjusting the reaction conditions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Sha Li, Yahan Sun, Xiaofang Li, Oskar Smaga, Sebastian Koniarz, Marcin Stepien, Piotr J. Chmielewski
Summary: A 1,3-cycloaddition reaction between 2-(tert-butyl)-8H-isoquinolino[4,3,2-de]phenanthridin-9-ium chloride and Ni-II norcorrole in the presence of base has been demonstrated to yield a family of chiral derivatives fused with pyrrole subunits of the macrocycle. Dehydrogenation of the cycloaddition products leads to dibenzoullazine ortho-fused antiaromatic porphyrinoids.
CHEMICAL COMMUNICATIONS
(2022)
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, Organic
Kazuki Nishimura, Yoshihiro Ogura, Kazuki Takeda, Weiwei Guo, Kazuaki Ishihara
Summary: A highly enantioselective alpha-amination reaction is reported, where N-acyl-3,5-dimethylpyrazoles react with dialkyl azodicarboxylates catalyzed by in situ generated pi-Cu(II) complexes. The corresponding D-alpha-amino acid derivatives are obtained with high yield and enantiopurity.
Article
Chemistry, Organic
Haruna Araki, Shohei Furuya, Kazuya Kanemoto, Shin-ichi Fukuzawa
Summary: The conjugated addition reaction of 1-pyrroline-5-carbonitrile to alpha-enones was effectively catalyzed by AgF/ThioClickFerrophos (TCF) in diethyl ether in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and nearly single diastereomers of adducts with good enantiomeric excesses (up to 97% ee) were obtained in high yields. The reduction of the nitrile group with H2/Raney Ni in ethanol successfully transformed the conjugate adduct to the corresponding spirocyclic piperidine (60% yield) as a single stereoisomer.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Zhenjie Gan, Ke Li, Hui Zhang, Er-Qing Li
Summary: A highly efficient copper/GanPhos-catalyzed 1,3-dipolar cycloaddition of azomethine ylides is reported in this study, providing optically active spiro[dihydronaphthalene-2,3'-pyrrolidine]s with one spiro quaternary and three tertiary stereogenic centers in good yields and high ee values. This protocol demonstrates high diastereo- and enantioselectivity, broad substrate scope, and mild reaction conditions.
SYNTHESIS-STUTTGART
(2021)
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, Multidisciplinary
Mohammed F. F. Radwan, Elghareeb E. E. Elboray, Hemat M. M. Dardeer, Yusuke Kobayashi, Takumi Furuta, Shohei Hamada, Toshifumi Dohi, Moustafa F. F. Aly
Summary: 1,3-Dipolar cycloaddition through in situ generation of azomethine ylide provides a straightforward and critically important sustainable approach for access to diverse pyrrolidine chemical space. Metal-free AcOH-activated 1,3-dipolar cycloaddition protocol was developed to synthesize uncommon pyrrolidine cycloadducts with excellent diastereoselectivity. The reaction mechanism and the key role of AcOH were supported by experimental, theoretical and spectroscopic studies.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Zi-Qi Yi, Bo-Wen Deng, Fei Chen, Yan-Mei He, Qing-Hua Fan
Summary: Highly efficient asymmetric hydrogenation of dibenzo[b,f][1,4]oxazepine, dibenzo[b,f][1,4]thiazepine and dibenzo[b,e]azepine derivatives was achieved using chiral cationic ruthenium diamine catalysts, affording diverse chiral seven-membered N-heterocycles with excellent results (up to 99% yield and 99% ee). Additionally, it was observed that the enantioselectivity in the hydrogenation of dibenzo[b,f][1,4]thiazepine and dibenzo[b,e]azepine derivatives could be significantly regulated by the catalyst counteranion.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Yoseop Kim, Seung Yeon Kim, Sung-Gon Kim
Summary: A new asymmetric annulation reaction was developed to efficiently synthesize enantioenriched polyheterotricyclic imidazolidines and oxazolidines.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Ulysse Caniparoli, Imma Escofet, Antonio M. Echavarren
Summary: Planar chiral monodentate 1,3-disubstituted ferrocene phosphines inspired by JohnPhos-type ligands have been synthesized and applied for the enantioselective gold(I) catalyzed [4 + 2] cycloaddition of 1,6-arylenynes. Computational studies elucidated the working mode of the catalyst, involving attractive noncovalent interactions that induce the folding of the substrate in the chiral environment of the ligand.
Article
Chemistry, Multidisciplinary
Alexander A. Penney, Mariia M. Efremova, Alexander P. Molchanov, Mariya A. Kryukova, Andrey Yu Kudinov, Alexander S. Bunev, Valentina M. Keresten, Mikhail A. Kuznetsov
Summary: Unsubstituted and 1-methyl-substituted 1,3,4,8b-tetrahydrodiazirino[3,1-a]isoquinolines exhibit different reactivities towards aryl isocyanates and aryl isothiocyanates.
Article
Chemistry, Organic
Takayuki Kudoh, Syo Fujisawa, Megumi Kitamura, Akira Sakakura
Article
Chemistry, Multidisciplinary
Manabu Hatano, Haruka Okamoto, Taro Kawakami, Kohei Toh, Hidefumi Nakatsuji, Akira Sakakura, Kazuaki Ishihara
Article
Chemistry, Organic
Haruka Okamoto, Kohei Toh, Takuya Mochizuki, Hidefumi Nakatsuji, Akira Sakakura, Manabu Hatano, Kazuaki Ishihara
SYNTHESIS-STUTTGART
(2018)
Article
Chemistry, Organic
Miyuki Terazaki, Kei-ichi Shiomoto, Haruki Mizoguchi, Akira Sakakura
Article
Chemistry, Organic
Ichiro Hayakawa, Ryosuke Nagatani, Masaki Ikeda, Dong-eun Yoo, Keita Saito, Hideo Kigoshi, Akira Sakakura
Article
Chemistry, Organic
Chihiro Kidou, Haruki Mizoguchi, Tatsuo Nehira, Akira Sakakura
Article
Chemistry, Organic
Ichiro Hayakawa, Anna Nagayasu, Akira Sakakura
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Yuya Araki, Natsumi Miyoshi, Kazuki Morimoto, Takayuki Kudoh, Haruki Mizoguchi, Akira Sakakura
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Takahiro Horibe, Shuhei Ohmura, Kei Katagiri, Kazuaki Ishihara
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Medicinal
Kana Shintani, Haruna Ebisu, Minagi Mukaiyama, Taisei Hatanaka, Takumi Chinen, Daisuke Takao, Yoko Nagumo, Akira Sakakura, Ichiro Hayakawa, Takeo Usui
ACS MEDICINAL CHEMISTRY LETTERS
(2020)
Article
Chemistry, Organic
Yudai Fujii, Ryota Nakao, Saki Sugihara, Keita Fujita, Yuya Araki, Takayuki Kudoh, Ichiro Hayakawa, Haruki Mizoguchi, Akira Sakakura
Article
Chemistry, Organic
Ichiro Hayakawa, Naochika Matsumaru, Akira Sakakura
Summary: The core scaffold of paspaline-type indole-terpenes was synthesized using the House-Meinwald rearrangement as a key step, successfully constructing contiguous asymmetric quaternary carbon centers.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Haruki Mizoguchi, Hidetoshi Kamada, Kazuki Morimoto, Ryuji Yoshida, Akira Sakakura
Summary: A stereoselective annulative coupling reaction that forms two C-C bonds and one C-B bond has been developed. This reaction utilizes a 1,2-metallate rearrangement of boronate triggered by the addition of a vinyl group to an aryne. The resulting annulated borinic ester can be converted to various boronic acids and their derivatives, with site-selective halogenation and Suzuki-Miyaura coupling reactions producing highly substituted alkylboronic acid derivatives.
Article
Chemistry, Multidisciplinary
Haruki Mizoguchi, Masaya Seriu, Akira Sakakura
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Yutaro Niwa, Mayu Miyake, Ichiro Hayakawa, Akira Sakakura
CHEMICAL COMMUNICATIONS
(2019)