Grant-in-Aid for Scientific Research on Innovative Areas FY2017-2021Hybrid Catalysis

Yujiro Hayashi » Japanese

Affiliation Tohoku University, Graduate School of Science
Position Professor
Contact Email
HP http://www.ykbsc.chem.tohoku.ac.jp/
Speciality Synthetic Organic Chemistry
Keyword Organocatalyst, Total synthesis
Institute Chemical Society of Japan, American Chemical Society, The Society of Synthetic Organic Chemistry, Japan

Abstract

Domino reaction is an environmentally friendly reaction, because several reactions can be carried out sequentially in the same vessel, and there is no need to isolate the intermediate, and the purification step between the reactions is omitted. Thus, it has advantages such as shortening of operation time and reduction of waste solvents. We have been investigating the domino reaction and one-pot reaction using organocatalyst. We already achieved three-pot synthesis of prostaglandin A1 and E1 methyl esters using the domino reaction, and one-pot synthesis of influenza treatment drug Tamiflu. In this research, we will focus on the development of the efficient domino reactions using organocatalyst. We aim to establish a new domino reaction of a carbon skeleton such as polysubstituted cyclopentanone, pyrrolidine, piperidine and nitrogen-containing heterocyclic skeleton, and investigated short-step synthesis of natural organic compounds having these skeletons.

Achievement

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Original papers

  • "Asymmetric Synthesis of Chiral 1,3-Dimethyl Units Through a Double Michael Reaction of Nitromethane and Crotonaldehyde Catalyzed by Diphenylprolinol Silyl ether"
    *Hayashi, Y; Toda, S.
    Synlett, 1/2019, 30, 442-448
  • "Asymmetrci Michael Reaction of Aldehydes and Dicyanoalkenes Catalyzed by Diphenylprolinol Silyl Ether"
    *Hayashi, Y.; Kranidiotis-Hisatomi, N.; Sakamoto, D.; Oritani, K.; Kawamoto, T.; Kamimura, A.
    Eur. J. Org. Chem., 11/6/2018, 6843-6847
  • "Domino Michael/Michael Reaction for the Formation of Chiral Spirocycles Using a Diphenylprolinol Silyl Ether"
    *Hayshi, Y.; Nagai, K.; Umemiya, S.
    Eur. J. Org. Chem., 9/20/2018, 678-681
  • "Asymmetric Michael reaction of aldehyde and -substituted -nitroacrylate catalyzed by diphenylprolinol silyl ether"
    Sakamoto, D.; *Hayashi, Y.
    Chem. Lett., 7/2018, 47(7), 833-835