个人简介

Education: B.Eng., Waseda University; M.Sc., Ph.D., The University of Tokyo

研究领域

Synthetic Organic Chemistry

Research Interest Development of New C-N Bond Forming Reactions Nitrogen containing organic molecules have attracted much attention as bioactive compounds and functional materials. In our group are currently focused on the chemical reactivity of some nitrogen-containing small molecules such as organic azides and oxime derivatives, and their chemical activation for generation of nitrogen reactive species like metal-nitrene complexes, iminyl metal species, and iminyl radicals. Such chemical species would lead to the development of unprecedented C-N bond forming reactions. The products synthesized by these reactions are especially important in medicinal, agricultural, and natural product chemistry as well as in the material science. For example, a Mn(III)-mediated divergent synthesis of substituted pyridines and 2-azabicyclo[3.3.1]non-2-en-1-ol derivatives was exploited using readily available vinyl azides and cyclopropanols with a wide range of substituents. The reactions of vinyl azides with monocyclic cyclopropanol provided pyridines in the presence of Mn(acac)3, whereas those with bicyclic cyclopropanols led to the formation of 2-azabicyclo[3.3.1]non-2-en-1-ol derivatives using a catalytic amount of Mn(acac)3. These reactions may be initiated by a radical addition of b-keto radicals, generated by the one-electron oxidation of cyclopropanols, to vinyl azides to give iminyl radicals, which would cyclize with the intramolecular carbonyl groups. Recently, a Pd(II)-catalyzed ring expansion-reaction of cyclic 2-azidoalcohol derivatives was found to proceed via unprecedented C-C bond cleavage–C-N bond formation sequence, providing substituted azaheterocycles. Synthesis of Natural and Unnatural Products We are interested in synthesis of natural and unnatural products bearing complex chemical structures as well as attractive biological activities and chemical properties. Some of current target molecules in our group are described below.

近期论文

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John Mondal, Anup Biswas, Shunsuke Chiba, Yanli Zhao. “Cu0 Nanoparticles Deposited on Nanoporous Polymers: A Recyclable Heterogeneous Nanocatalyst for Ullmann Coupling of Aryl Halides with Amines in Water”. Sci. Rep. 2015, in press (DOI: 10.1038/srep08294) Ya Lin Tnay and Shunsuke Chiba. “Cu-Catalyzed Aerobic C-C Bond Cleavage of Lactols with N-Hydroxy Phthalimide for Synthesis of Lactones”. Chem. Asian J. 2015, 10, in press (DOI: 10.1002/asia.201403196). Xiaoling Wang, Ming Keat Sng, Selin Foo, Han Chung Chong, Wei Li Lee, Mark Boon Yang Tang, Kee Woei Ng, Baiwen Luo, Cleo Choong, Marcus Thien Chong Wong, Benny Meng Kiat Tong, Shunsuke Chiba, Say Chye Joachim Loo, Pengcheng Zhu, and Nguan Soon Tan. “Early controlled release of PPARβ/δ agonist GW501516 improves diabetic wound healing through redox modulation of wound microenvironment”. J. Control. Rel. 2015, 197, 138-147. Hui Chen, Atsushi Kaga, and Shunsuke Chiba. “Diastereoselective Aminooxygenation and Diamination of Alkenes with Amidines by Hypervalent Iodine(III) Reagents”. Org. Lett. 2014, 16, 6136-6139. Yi-Feng Wang, Geoffroy Hervé Lonca, Maïwenn Le Runigo, and Shunsuke Chiba. “Synthesis of Polyfluoroalkyl Aza-Polycyclic Aromatic Hydrocarbons Enabled by Addition of Perfluoroalkyl Radicals onto Vinyl Azides”. Org. Lett. 2014, 16, 4272-4275. Xu Zhu and Shunsuke Chiba. “TEMPO-Mediated Allylic C-H Amination with Hydrazones”. Org. Biomol. Chem. 2014, 12, 4567-4570. Xu Zhu, Yi-Feng Wang, Feng-Lian Zhang, and Shunsuke Chiba. “Formal [4+2]-Annulation of Vinyl Azides with N-Unsaturated Aldimines”. Chem. Asian J. 2014, 9, 2458. Kah Kah Toh, Anup Biswas, Yi-Feng Wang, Yun Yun Tan, and Shunsuke Chiba. “Copper-Mediated Oxidative Transformation of N-Allyl Enamine Carboxylates for Synthesis of Azaheterocycles”. J. Am. Chem. Soc. 2014,134, 6011-6020. Feng-Lian Zhang, Yi-Feng Wang, Geoffroy Hervé Lonca, Xu Zhu, and Shunsuke Chiba. “Amide Synthesis by Nucleophilic Attack of Vinyl Azides”. Angew. Chem. Int. Ed. 2014, 53, 4390-4394. Xingao Peng, Benny Meng Kiat Tong, Hajime Hirao, and Shunsuke Chiba. “Inorganic Base-Mediated Hydroamination of Alkenyl Oximes for the Synthesis of Cyclic Nitrones”. Angew. Chem. Int. Ed. 2014, 53, 1959-1962. Yi-Feng Wang, Geoffroy Hervé Lonca, and Shunsuke Chiba. “PhI(OAc)2-Mediated Radical Trifluoromethylation of Vinyl Azides with Me3SiCF3”. Angew. Chem. Int. Ed. 2014, 53, 1067-1071. Hui Chen and Shunsuke Chiba. “Copper-Catalzyed Redox-Neutral C-H Amination with Amidoximes”. Org. Biomol. Chem. 2014, 12, 42-46. Jian Zhang, Yu Liu, Shunsuke Chiba, and Teck-Peng Loh. “Chemical Conversion of β-O-4 Lignin Linkage Models through Cu-Catalyzed Aerobic Amide Bond Formation”. Chem. Commun. 2013, 49, 11439-11441. Feng-Lian Zhang, Yi-Feng Wang, and Shunsuke Chiba. “Orthogonal Aerobic Conversion of N-Benzyl Amidoximes to 1,2,4-Oxadiazoles or Quinazolinones”. Org. Biomol. Chem. 2013, 11, 6003-6007. Pei Chui Too, Ya Lin Tnay, and Shunsuke Chiba. “Copper-Catalyzed Aerobic Aliphatic C-H Oxygenation with Hydroperoxides”. Beilstein J. Org. Chem. 2013, 9, 1217-1225. Xu Zhu, Yi-Feng Wang, Wei Ren, Feng-Lian Zhang, and Shunsuke Chiba. “TEMPO-Mediated Aliphatic C-H Oxidation of Oximes and Hydrazones”. Org. Lett. 2013, 15, 3214-3217. Yi-Feng Wang, Feng-Lian Zhang, and Shunsuke Chiba. “Oxidative Radical Skeletal Rearrangement Induced by Molecular Oxygen: Synthesis of Quinazolinones”. Org. Lett. 2013, 15, 2842-2845. Pengcheng Zhu, Benny Meng Kiat Tong, Runze Wang, Kelvin Jiapeng Chen, Selin Foo, Han Chung Chong, Xiao Ling Wang, Gim Yean Ang, Shunsuke Chiba, and Nguan Soon Tan. “Nox4-dependent ROS modulation by amino endoperoxides to induce apoptosis in cancer cells”. Cell Death & Disease 2013, 4, e552. Hui Chen, Stephen Sanjaya, Yi-Feng Wang, and Shunsuke Chiba. “Copper-Catalyzed Aliphatic C-H Amination with an Amidine Moiety”. Org. Lett. 2013, 15, 212-215.