Effective chiral thiophene diamine derivatives in Pd-catalyzed enantioselective allylic alkylation

Bulletin of the Korean Chemical Society

Volumn 25, Issue 5, 2004, Pages 754-756

  Kim, Sang Han ^a   Lee, Eun Kyung ^a   Kim, Geon Joong ^a  

^a Inha University   (South Korea)

Author keywords

Allylic alkylation; Pd catalyzed; Thiophene diamines

Indexed keywords

DIAMINE DERIVATIVE; PALLADIUM; THIOPHENE DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 3242655783     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2004.25.5.754     Document Type: Article

References (19)

1. (a) Tsuji, J. Transition Metals in Organic Synthesis; Kagaku Dojin: Japan, 1997.
2. (b) Tsuji, J. Palladium Reagents and Catalysts, Innovations in Organic Synthesis; John Wiley: 1995; p 290.
3. (c) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. J. Am. Chem. Soc. 1992, 114, 9327.
4. (d) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089.
5. (e) Trost, B. M.; Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104.
6. (a) Togni, A.; Venanzi, L. M. Angew. Chem. Int. Ed. Engl. 1994, 33, 497.
7. (b) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
8. (c) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1.
9. (a) Nishibayashi, Y.; Segawa, K.; Takada, H.; Ohe, K.; Uemura, S. Chem. Commun. 1996, 847.
10. (b) Pretot, R.; Pfaltz, A. Angew. Chem. Int. Ed. Engl. 1998, 37, 323.
11. Saito, A.; Morimoto, T.; Achiwa, K. Tetrahedron; Asymmetry 1997, 8, 3567.
12. Lee, S. G.; Lee, S. H.; Song, C. E.; Chung, B. Y. Tetrahedron; Asymmetry 1999, 10, 1795.
13. Anderson, J. C.; James, D. S.; Mathias, J. P. Tetrahedron; Asymmetry 1998, 9, 753.
14. Frost, C. G.; Williams, J. M. J. Tetrahedron Lett. 1993, 34, 2015.
15. 4, filtered off, and solvent removed under reduced pressure. The crude product was purified by flash column chromatography. The conversion was determined by GC analysis and the enantiomeric excess was determined by HPLC analysis (Chiralcel OD-H column; n-hexane:2-propanol = 99:1; flow rate, 0.5 mL/min).
16. (a) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149.
17. (b) Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 3047.
18. 3); IR (KBr) 3300, 2930, 2790, 1450, 1340, 825 and 690.
19. Kim, Y. K.; Lee, S. J.; Ahn, K. H. J. Org. Chem. 2000, 65, 7807.