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
Speciality Synthetic Organic Chemistry
Keyword Organocatalyst, Total synthesis
Institute Chemical Society of Japan, American Chemical Society, The Society of Synthetic Organic Chemistry, Japan


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.


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Original papers

  • "Pot-Economical Total Synthesis of Clinprost"
    Umekubo, N.; *Hayashi, Y.
    Org. Lett., 22, 9365-9370
  • "Asymmetric Domino Reaction of-Unsaturated Aldehydes and -Acyl -Unsaturated Cyclic Ketones Catalyzed by Diphenylprolinol Silyl Ether"
    *Hayashi, Y.; Suga, Y.; Umekubo, N.
    Org. Lett., 22, 8603-8607
  • "Evidence for an enolate mechanism in the asymmetric Michael reaction of -unsaturated aldehydes and ketones via a hybrid system of two secondary amine catalysts"
    Umekubo, N.; Terunuma, T.; Kwon, E.; *Hayashi, Y.
    Chem. Sci. , 11, 11293-11297
  • "214. Asymmetric Synthesis of Corey Lactone and Latanoprost"
    Umekubo, N.; *Hayashi, Y.
    Eur. J. Org. Chem., 6221-6227
  • "Asymmetric One-Pot Mukaiyama Michael/Michael reaction catalyzed by diphenylprolinol silyl ether"
    Umekubo, N.; Hayashi, Y.
    Eur. J. Org. Chem., 5596-5600
  • "Highly Enantioselective Access to syn-α, γ-Dihydroxycarbonyl Building Blocks via Organocatalyst-Mediated Aldol Reaction as a Key Step"
    *Hayashi, Y.; Wang, X.; Kawauchi, G.
    Chem. Lett., 49, 940-943
  • "One-pot synthesis of chiral cis-hydrindanes via diphenylprolinol silyl ether mediated domino reaction and aldol condensation"
    Umekubo, N.; Iwata, R.; Hayashi, Y.
    Chem. Lett., 49, 867-869
  • "Asymmetric Michael reaction of aldehydes and α-cyano α, β-unsaturated esters catalyzed by diphenylprolinol silyl ether; a facile asymmetric route to 3,4,5-trisubstituted piperidines"
    *Hayashi, Y.; Odoh, A. S.; Kranidiotis-Hisatomi, N.
    ChemCatChem, 12, 2412-2415
  • "Inversion of the Axial Information during Oxidative Aromatization in the Synthesis of Axially Chiral Biaryls with Organocatalysis as a Key Step"
    Koshino, S.; Takikawa, A.; Ishida, K.; Taniguchi, T.; Monde, K.; Kwon, E.; Umemiya, S.; *Hayashi, Y.
    Chem. Eur. J., 26, 4525-4530
  • "Pot and time economies in the total synthesis of Corey lactone"
    Umekubo, N.; Suga, Y., *Hayashi, Y.
    Chem. Sci., 11, 1205-1209
  • "Pot and time economies in the total synthesis of Corey lactone,"
    Umekubo, N.;Suga, Y.; Hayashi, Y.
    Chem. Sci., 12/23/2019, 11, 1205-1209
  • "Asymmetric Synthesis of Biaryl Atropisomers Using an Organocatalyst-Mediated Domino Reaction as the Key Step"
    Hayashi, Y.;Takikawa, A.;Koshino, S.;Ishida, K.
    Chem. Eur. J., 6/19/2019, 21, 10319-10322
  • "Asymmetirc Michael Reaction of -CF3 Thioester and -Unsaturated Aldehyde Catalyzed by Diphenylprolinol Silyl Ether"
    Hayashi, Y.;Yamda, T.; Sato, M.;Watanabe, S.;Kwon, E.;Iwasaki, K.;Umemiya, S.
    Org. Lett. , 6/18/2019, 21, 5183-5186
  • "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