DOI QR코드

DOI QR Code

Catalytic Asymmetric Allylic Alkylation with A Novel P-S Bidentate Ligand


Abstract

Both enantiomers of (S)-(-)-2-(diphenylphosphino)-2'-mercapto-1,1'-binaphthyl and their derivatives were obtained by synthesis from racemic 2,2'-dihydroxy-1,1'-binaphthyl and subsequent resolution. The utilities of these ligands were investigated briefly. And among these, S-methyl derivative 15 has proved to be an effective ligand for Pd-catalyzed allylic alkylation.

Keywords

References

  1. J. Chem. Soc., Chem. Commun. Jedlicka, B.;Kratky, K.;Weissensteiner, W.;Widhalm J.M.
  2. Angew. Chem. Int. Ed. Engl. v.32 Reiser, O.
  3. Tetrahedron Lett. v.34 Helmchen, G.;Sprinz, J.
  4. Tetrahedron Lett. v.34 Williams, J.M.J.;Dawson, G.J.;Frost, C.G.
  5. Angew. Chem. Int. Ed. Engl. v.32 Pfaltz, A.;Matt, P.
  6. Tetrahedron Lett. v.34 Williams, J.M.J.;Frost, C.G.
  7. Tetrahedron: Asymmetry v.4 Williams, J.M.J.;Frost, C.G.
  8. J. Am. Chem. Soc. v.113 Hayashi, T.;Uozumi, Y.
  9. Tetrahedron Lett. v.33 Hayashi, T.;Uozumi, Y.;Lee, S.Y.
  10. J. Am. Chem. Soc. v.115 Takaya, H.;Sakai, N.;Mano, S.;Nozaki, K.
  11. Synthesis Rosini, C.;Franzini, A.;Raffaelli, A.;Salvadori, P.
  12. Inorg. Chem. v.31 Wild, S.B.;Leung, P.H.;Willis, A.C.
  13. J. Chem. Soc., Chem. Commun. Kang, J.;Lee, J.W.;Kim, J.I.
  14. Synlett Kang, J.;Kim, D.S.;Kim, J.I.
  15. manuscript in preparation Kang, J.;Lee, J.W.;Kim, J.I.;Kim, D.S.;Kim, J.W.
  16. Tetrahedron:Asymmetry v.5 Gladiali, S.;Dore, A.;Fabbri, D.
  17. J. Org. Chem. v.58 Hayashi, T.;Uozumi, Y.;Tanahashi, A.;Lee, S.Y.
  18. Tetrahedron Lett v.31 Ward, T.;Kurz, L.;Lee, G.;Morgans, D.;Waldyke, M.J.
  19. J. Org. Chem. v.43 Cram, D.J.;Helgeson, R.C.;Koga, K.;Kyba, E.P.;Modan, K.;Sousa, L.R.;Siegel, M.G.;Moreau, P.;Gokel, G.W.;Timko, J.M.;Sogah, D.Y.
  20. Tetrahedron Lett v.35 Helmchen, G.;Sprinz, J.;Kiefer, M.
  21. Tetrahedron:Asym. v.5 Kang, J.;Cho, W.O.;Cho, H.G.

Cited by

  1. ChemInform Abstract: Catalytic Asymmetric Allylic Alkylation with a Novel P-S Bidentate Ligand. vol.26, pp.46, 1995, https://doi.org/10.1002/chin.199546112
  2. Chiral Complexes of RhI Containing Binaphthalene-Core P,S-Heterobidentate Ligands − Synthesis, Characterization, and Catalytic Activity in Asymmetric Hydrogenation of α,β-U vol.2003, pp.3, 1995, https://doi.org/10.1002/ejic.200390077
  3. Binaphthalene-templated N,S- and N,P-heterobidentate ligands with an achiral oxazoline pendant : Synthesis and assessment in asymmetric catalysis vol.196, pp.1, 1995, https://doi.org/10.1016/s1381-1169(02)00632-5
  4. Thioether containing ligands for asymmetric allylic substitution reactions vol.10, pp.3, 2007, https://doi.org/10.1016/j.crci.2007.01.004
  5. Recent developments on chiral P,S-type ligands and their applications in asymmetric catalysis vol.46, pp.26, 1995, https://doi.org/10.1039/c000207k
  6. Atroposelective synthesis of axially chiral P,S-ligands based on arynes vol.2, pp.6, 1995, https://doi.org/10.1039/c5qo00067j
  7. Evolution of phosphorus-thioether ligands for asymmetric catalysis vol.56, pp.74, 1995, https://doi.org/10.1039/d0cc04145a