Article
Biochemistry & Molecular Biology
Kosuke Yamamoto, Keisuke Miyamoto, Mizuki Ueno, Yuki Takemoto, Masami Kuriyama, Osamu Onomura
Summary: In this study, glycerol was efficiently transformed into optically active monosulfonylated glycerol using a specific catalyst system. The synthetic utility of the monosulfonylated glycerol was demonstrated by its transformation into a C3 unit with differentially protected three hydroxy moieties.
Article
Chemistry, Organic
Yanting Li, Xiao-Yong Duan, Chengxian Yang, Yamei Wei, Jiahan Li, Xiaojie Ren, Jing Qi
Summary: This article describes a N-heterocyclic carbene-catalyzed atroposelective [3+3] annulation of enals with 2-aminomaleate derivatives. A series of substituted dihydropyridones with both C-N axis and point chirality were synthesized with good diastereo- and enantioselectivity under mild conditions. This efficient strategy introduces an additional point chiral element to an axial backbone, and the resulting structurally interesting atropisomers may have potential applications in drug discovery.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Shrikant D. Tambe, Cheol Hyeon Ka, Ho Seong Hwang, Jaehan Bae, Naeem Iqbal, Eun Jin Cho
Summary: The synthesis of highly functionalized chiral 3-pyrrolines is important for the production of natural and synthetic bioactive molecules. Previous methods using allenoates could not synthesize 3,4-disubstituted 3-pyrrolines. This study presents a novel approach to produce 2,3,4-trisubstituted chiral 3-pyrrolines through a highly stereoselective process using a Ni-II/Fc-i-PrPHOX catalytic system.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Sibin Wang, Oleksii Zhelavskyi, Jeonghyo Lee, Alonso J. Arguelles, Yaroslav Ya Khomutnyk, Enoch Mensah, Hao Guo, Rami Hourani, Paul M. Zimmerman, Pavel Nagorny
Summary: This article describes studies on regioselective acetal protection of monosaccharide-based diols using chiral phosphoric acids as catalysts, showing high regioselectivities and the ability for regiodivergent reactions. The polymeric catalysts are convenient for recycling and the computational studies reveal complex temperature-dependent reaction mechanisms. These catalyst-controlled reactions demonstrate superior performance and the ability to produce diverse derivatives with different protection patterns.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Physical
Liangliang Zhang, Martin Oestreich
Summary: The passage describes a reaction sequence involving enantioselective copper-catalyzed conjugate silylation and diastereotopic group-selective aldol cyclization. The intramolecular aldol reaction's diastereoselectivity depends on the silicon nucleophile used, and the more basic zinc reagent enables thermodynamically driven cis-to-trans isomerization. A wide range of electron-withdrawing groups, including electron-deficient heterocycles, are compatible with the different procedures developed.
Article
Chemistry, Organic
Xinpeng Cheng, Liming Zhang
Summary: This work describes an asymmetric gold-ligand cooperative catalysis for the transformation of readily accessible chiral/achiral propargylic sulfonamides into chiral 3-pyrrolines. A bifunctional biphenyl-2-ylphosphine ligand containing a chiral tetrahy-droisoquinoline fragment is crucial for the observed metal-ligand cooperation and asymmetric induction. The reaction can provide 2,5-cis-3-pyrrolines with excellent diastereoselectivities in a matched scenario, and 2,5-trans-3-pyrrolines with >5/1 diastereoselectivity in a mismatched scenario using the ligand enantiomer. The synthetic utilities of this chemistry have been demonstrated.
Article
Chemistry, Organic
Jih Ru Hwu, Avijit Panja, Nitesh K. Gupta, Wen-Chieh Huang, Yu-Chen Hu, Chun-Cheng Lin, Kuo-Chu Hwang, Wei-Jen Chan, Shwu-Chen Tsay
Summary: The synthesis of optically active 3-pyrrolines through a newly developed domino reaction using a chiral catalyst showed high stereo- and enantio-selectivity, with a single product generated in good yields. The reaction also involved an aryne-induced domino reaction and an unusual 1,4-intramolecular proton transfer, demonstrating high enantiomeric ratios up to 98.5:1.5.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Debraj Ghorai, Kanak Kanti Das, Santanu Panda
Summary: In this study, a transition metal-free carbonyl-directed boron-Wittig reaction method was used to synthesize alkenyl oxindoles using alpha-bis(boryl)carbanions as substrates. The reaction showed high selectivity and allowed for specific substitution patterns. This method has significant research and application value.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Raj Kumar Patel, Anil Chauhan, Priyankar Jha, Ruchir Kant, Ravindra Kumar
Summary: A new strategy has been developed for the synthesis of linear and bridged polycyclic pyrroles with high selectivity, and it has also been demonstrated to be effective for the synthesis of 3-arylpyrroles. The experimental results showcase the reliability and wide applicability of this method.
Article
Chemistry, Organic
Xiaoxue Tang, Zhishan Su, Liqiao Yan, Qiong Tang, Shunxi Dong, Lili Lin, Xiaoming Feng
Summary: Highly diastereo- and enantioselective allylation of isatins with 3-substituted allylboronic compounds was achieved using the chiral N,N'-dioxide/Lu(OTf)(3) complex, leading to enantioenriched 3-allyl-3-hydroxyoxindoles with adjacent tetrasubstituted tertiary or tetrasubstituted quaternary stereogenic centers. The synthetic utility of the reaction was demonstrated by further transformation of the product to a tetrahydrofuranyl oxindole derivative.
Article
Chemistry, Organic
Takeshi Yamamoto, Michinori Suginome, Ryo Murakami
Summary: PQXdpap exhibits different helical chirality switching under different solvent conditions and can effectively prepare enantiomerically pure alcohol compounds.
Article
Chemistry, Physical
Francisxavier Paularokiadoss, Thiruthuvadevaraj Antony Sandosh, Alagan Sekar, Thayalaraj Christopher Jeyakumar
Summary: The reaction and electronic structural analysis of transition metal carbonyls and corresponding gallylene complexes were investigated theoretically. Orbital interactions between metal and gallium, as well as the formation order of bonds, were analyzed. The feasibility of complexes formation through a five-member coordinated transition state was confirmed.
COMPUTATIONAL AND THEORETICAL CHEMISTRY
(2021)
Article
Multidisciplinary Sciences
Sandip B. Jadhav, Soumya Ranjan Dash, Sundaram Maurya, Jagadeesh Babu Nanubolu, Kumar Vanka, Rambabu Chegondi
Summary: The authors present a tandem copper-catalyzed reaction for the synthesis of bicyclic borylated compounds with high yield and enantioselectivity. This method combines beta-borylation and Michael addition reactions on specific prochiral enone-tethered compounds. The asymmetric desymmetrization strategy used in this reaction allows for the synthesis of densely functionalized bicyclic enones with multiple stereocenters.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Xiang-Shuai Liu, Yao Li, Xin Li
Summary: A highly efficient asymmetric 1,2-allylation reaction of beta,gamma-unsaturated alpha-ketoesters was achieved using a Bi(OAc)(3)/chiral phosphoric acid catalyst system under mild conditions. Additionally, an asymmetric formal 1,4-allylation reaction was realized through a one-pot process, yielding homoallylic tertiary alcohols and gamma-allyl-alpha-ketoesters with good yields and excellent enantioselectivities. Density functional theory calculations were used to interpret the high enantioselectivity observed in the reactions.
Article
Biochemistry & Molecular Biology
Kobra Nikoofar, Narges Saheb Ekhtiari
Summary: A new multilayered magnetized bio-nanocomposite was prepared and characterized using various techniques. The core-shell nanostructure showed catalytic activity in a three-component reaction, demonstrating eco-friendly features and reusability. The research highlights the potential of the bio-nanocomposite in organic transformations under benign conditions.
MOLECULAR DIVERSITY
(2022)
Article
Chemistry, Organic
Ichiro Hayakawa, Yuji Yamanaka, Koichi Mitsudo, Hiromi Ota, 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)
