화학공학소재연구정보센터
Journal of Industrial and Engineering Chemistry, Vol.12, No.4, 643-647, July, 2006
Polymer-Supported Heterogeneous Chiral Ligands for Palladium- Catalyzed Asymmetric Allylic Alkylation
E-mail:
Chiral thiophene derivatives prepared from enantiomerically pure (R,R)-1,2-diaminocyclohexane were successfully immobilized onto insoluble polymer support. The polymer-supported heterogeneous chiral ligands showed moderate reactivity and enantioselectivity (up to 71 %ee) in the palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate, the enantioselectivity was maintained when the catalysts were recycled and reused two times without any radical loss.
  1. Togni A, Venanzi LM, Angew. Chem.-Int. Edit. Engl., 33, 498 (1994)
  2. Bhalay G, Dunstan A, Glen A, Synlett, 12, 1846 (2000)
  3. Steiner I, Aufdenblatten R, Togni A, Blaser HU, Pugin B, Tetrahedron: Asymmetry, 15, 2307 (2004)
  4. Lesma G, Danieli B, Passarella D, Sacchetti A, Silvani A, Tetrahedron: Asymmetry, 14, 2453 (2003)
  5. Trost BM, Vanvranken DL, Chem. Rev., 96(1), 395 (1996)
  6. Adams H, Anderson JC, Cubbon R, James DS, Mathias JP, J. Org. Chem., 64, 8256 (1999)
  7. Evans DA, Campos KR, Tedrow JS, Michael FE, Gagne MR, J. Am. Chem. Soc., 122(33), 7905 (2000)
  8. Kim SH, Oh SS, Kim SH, Kim GJ, J. Ind. Eng. Chem., 11(4), 522 (2005)
  9. Nakano H, Okuyama Y, Yanagida M, Hongo H, J. Org. Chem., 66, 620 (2001)
  10. Trost BM, Weber L, Strege PE, Fullerton TJ, Dietsche T, J. Am. Chem. Soc., 100, 3435 (1978)
  11. von Matt P, Pfaltz A, Angew. Chem.-Int. Edit. Engl., 32, 566 (1993)