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Bifunctional catalysts

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Bifunctional catalysts

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  1. Masakatsu Shibasaki was born in 1947 in Japan. In 1974 he received his Ph. D. Degree from the University of Tokyo. After then he did postdoctoral studies with professor E. J. Corey at Harvard University. In 1977, he returned to Japan and joined Teikyo University as an associate professor. In 1983 he moved to Sagami Chemical Research Center as a group leader and in 1986 took up a professorship at Hokkaido University, before returning to the University of Tokyo as a professor in 1991.His research interests include asymmetric catalysis and medicinal chemistry of biologically significant compounds. • He has received Fluka Prize( 1996), the Elsevier Award for Inventiveness in Organic Chemisty(1998), the Pharmaceutical Society of Japan Award(1999), ACS Award (2002), the National prize of Purple Ribbon(2003), Japan Academy Prize(2005), t he Rare Earth Society of Japan Award(2006), ACS Award for Creative Work in Synthetic Organic Chemisty(2008), Centenary medal and lectureship (2008), Prelog Award Medal(2008), and many others.

  2. Bifunctional catalysts Advantage：Mild Reaction Condition Enhanced Catalytic Activity Higer Levels of Stereodifferentiation

  3. Shibasaki,M. J. Am. Chem. Soc.1993, 115, 10372

  4. Bimetallic Schiff Base catalysts

  5. Bimetallic Schiff Base catalystsM1=Cu M2=Sm

  6. Shibasaki,M. J. Am. Chem. Soc. 2010, 132, 4925. Shibasaki, M. J. Am. Chem. Soc. 2007, 16, 4900.

  7. M1=Pd M2=La Shibasaki, M. etal. Ang. Chem. Ind. Ed.2008, 47, 3230. Shibasaki, M. etal. Org. Lett. 2008, 10, 2231.

  8. M1=M2=Ni Shibasaki, M. J. Am. Chem. Soc. 2008, 130,2171.

  9. M1=M2=Mn Shibasaki, M. J. Am. Chem. Soc. 2009, 131,9169.

  10. first organacatalytic enantioseletive amination of oxindoles Chen, Y.-J. Org. Lett. 2009,11, 3874. Disadvantage:1, 10 mol % catalyst was required. 2, only 3-benzyl type substituted oxindoles afforded than 90% ee. 3, the key N-N cleavage of amination adduts was not reported.

  11. Shibasaki, M. J. Am. Chem. Soc.2010, 132, 1255.

  12. Shibasaki, M. J. Am. Chem. Soc.2010, 132, 3666.. dr >30:1 up to 99% ee Direct catalytic asymmetric vinylogous reactions of an α,β-unsaturated γ-butyrolactam as a donor are described. A homodinuclear Ni2-Schiff base complex promoted a vinylogous Mannich-type reaction of N-Boc imines as well as a vinylogous Michael reaction to nitroalkenes selectively at the γ-position under simple proton-transfer conditions. Vinylogous Mannich adducts were obtained in 5:1→30:1 dr and 99% ee, and vinylogous Michael adducts were obtained in 16:1→30:1 dr and 93−99% ee. dr>30:1 up to 99% ee

  13. M1=Ga,M2=Yb ee 50%-80％ Zhu, J., Org. Lett. 2007, 9, 3615. Shibasaki, M. J. Am. Chem. S. 2009, 131, 8384.

  14. Possible Reaction Mechanisum

  15. M1=M2=Co First Enantioseletive Conjugate to Alkyones Jфrgensen, K. A. J. Am. Chem. Soc.2004, 26, 5672. Maruoka, K., J. Am. Chem. Soc.2007, 129, 1038.

  16. Shibasaki, M. Ang. Chem. Int. Ed. 2009, 48, 2218.

  17. Postulated catalytic cycle of the Reaction Shibasaki, M. Molecules, 2010, 15, 532.

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