Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

The Interaction of Chiral Amino Thiols with Organozinc Reagents and Aldehydes: A Mechanism of Amino Thiol-Catalyzed Addition of Organozinc Reagents to Aldehydes

  • Published : 1998.04.20
Download PDF
⟨ Previous Next ⟩

Abstract

Details of various equilibria involved in the reactions of oxaza- and thiazazincolidine catalysts, generated from either β-amino alcohol or β-amino thiol, with aldehyde were studied by colligative measurements. The results indicated that the coordination of diethylzinc prior to the coordination of aldehyde is essential for high enantioselectivity of the thiol catalyzed reaction. The probable origin of asymmetric nonlinearity is also presented.

Keywords

References

  1. Angew, Chem. Int. Ed. v.30 Noyori, R.;Kitamura, M.
  2. Chem. Rev. v.92 Soai, K.;Niwa, S.
  3. J. Am. Chem. Soc. v.110 Oguni, N.;Matsuda, Y.;Kaneko, T.
  4. Tetrahedron: Asymmetry v.4 Hones, G. B.;Heaton, S. B.
  5. J. Am. Chem. Soc. v.108 Kitamura, M.;Suga, S.;Kawai, K.;Noyori, R.
  6. J. Am. Chem. Soc. v.109 Soai, K.;Okawa, A.;Kaba, T.;Ogawa, K.
  7. J. Am. Chem. Soc. v.111 Kitamura, M.;Okada, S.;Suga, S.;Noyori, R.
  8. J. Phys. Chem. v.98 Kitamura, M.;Suga, S.;Niwa, M.;Noyori, R.;Zhai, Z.-X.;Suga, H.
  9. J. Am. Chem. Soc. v.117 Kitamura, M.;Suga, S.;Niwa, M.;Noyori, R.
  10. Tetrahedron: Asymmetry v.6 Fitzpatrick, K.;Hulst, R.;Kellogg, R. M.
  11. J. Chem. Soc., Chem. Commun. v.2009 Kang, J.;Lee, J. W.;Kim, J. I.
  12. Synlett v.842 Kang, J.;Kim, D. S.;Kim, J. I.
  13. J. Chem. Soc., Perkin 2 v.189 Kang, J.;Kim, J. B.;Kim, J. W.;Lee, D.
  14. J. Am. Chem. Soc. v.116 Guillaneus, D.;Zhao, S. H.;Samuel, O.;Rainford, D.;Kagen, H. B.