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Synthetic Organic Chemistry

To the Laboratory Site(Under Construction)


Staffs

  Toyohiko Aoyama, Ph. D., Professor
Kazuhiro Kondo, Ph. D., Associate Professor

Research Project

 
Development of Organosilicon Reagents and Their Application to Organic Synthesis
Development of Chiral Ligands for Asymmetric Reactions
Development of Organocatalysts

Synthetic organic chemistry is a fascinating and vital area of modern chemistry. It produces a funny adventure since it offers intellectual excitement and challenges, and one can create a new universe by doing synthetic organic chemistry. Furthermore, it will constitute the first step for the creation of novel medicines.
Although synthetic organic chemistry has now rapidly progressed, yet how inferior are our methods compared with those of the life process. Thus, exploitation of new methods and new reagents in addition to new principles of organic synthesis are needed. Our research interests focus on exploitation of new methods and new reagents in organic synthesis and we have already developed several versatile synthetic reagents, eg., trimethylsilyldiazomethane (Me3SiCHN2) and trimethylsilylketene (Me3SiCH=C=O). Additionally, Organic syntheses aiming at the recent demands such as social contribution, atom-economy and safety, have been aggressively studied.
(1) Synthetic applications of Me3SiCHN2 and Me3SiCH=C=O: Me3SiCHN2 is a stable and safe substitute for hazardous diazomethane and acts as a C1-unit introducer and a [C-N-N]azole synthon. Moreover, Me3SiCHN2 can be used for the generation of alkylidenecarbene species from carbonyl compounds. Meanwhile, Me3SiCH=C=O is a stable and safe substitute for hazardous ketene, as a building block for heterocycles. [Tetrahedron Lett. 2006, 47, 1137 and Tetrahedron Lett. 2007, 48, 7019]
(2) Asymmetric Ni-catalyzed arylation and allylation of carbonyl and imino compounds: The reaction is one of the most important C-C bond-forming reactions, because chiral sec-methanols are important intermediates for the synthesis of biologically active compounds. From the viewpoint of cost and practical convenience, we have focused on the use of a much cheaper and more naturally abundant metal catalyst, Ni, than Rh and Pd in order to develop the title reactions. [Tetrahedron Lett. 2007, 48, 4115]
(3) Chiral hemilabile phosphine or N-heterocyclic carbene ligands: We have developed new hemilabile phosphine ligands with both soft and hard coordinated centers within one molecule, and carbene ligands mimicking chiral center in which a chiral carbon center induces a preferred conformation, which is fixed by formation of a chelate structure with metal. [Synthesis 2006, 3809 and Tetrahedron Lett. 2006, 47, 1417]
(4) Construction of tetra-substituted carbon by organocatalyst: We have developed new methods for cyanation reaction, etc of lower reactive ketones and ketimines than aldehydes and aldimines in the presence of a organocatalyst. [Synthesis 2006, 2649]

Contact Information

  Graduate School of Pharmaceutical Sciences, Nagoya City University,
3-1, Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan

TEL/FAX:+81-52-836-3439
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