Palladium-catalyzed enantioselective synthesis of cyclohexene derivatives via kinetic resolution

Tetrahedron Letters

Volumn 40, Issue 31, 1999, Pages 5713-5716

  Nishimata, Toyoki ^a   Yamaguchi, Kentaro ^b   Mori, Miwako ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

( Allyl)palladium complex; (S) BINAPO; Asymmetric synthesis; Kinetic resolution; Pd2dba CHCl3

Indexed keywords

AMIDE; CARBONIC ACID DERIVATIVE; CYCLOHEXENE DERIVATIVE; LIGAND; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0033618303     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01079-5     Document Type: Article

References (12)

1. 1. Recent reviews: (a) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993 and references cited therein.
2. (b) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395 and references sited therein.
3. (a) Mori, M.; Kuroda, S.; Zhang, C.-S.; Sato, Y. J. Org. Chem. 1997, 62, 3263.
4. (b) Nishimata, T.; Mori, M. J. Org. Chem. 1998, 63, 7586.
5. 3 and 3b in THF to give (S)-2a.
6. (a) Hayashi, T.; Yamamoto, A.; Ito, Y. J. Chem. Soc., Chem. Commun. 1986, 1090.
7. (b) Gais, H.-J.; Eichelmann, H.; Spalthoff, N.; Gerhards, F.; Frank, M.; Raabe, G. Tetrahedron: Asymmetry 1998, 9, 235.
8. (c) Lloyd-Jones, G. C.; Stephen, S. C. J. Chem. Soc., Commun. 1998, 2321.
9. (d) Ramdeehul, S.; Dierkes, P.; Aguado, R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Osborn, J. A. Angew. Chem. Int. Ed. 1998, 37. 3118.
10. (e) Trost, B. M.; Hembre, E. J. Tetrahedron Lett. 1999, 40, 219.
11. 6S: C. 64.39; H, 7.40; N, 2.78; S. 6.37. Found: C, 64.35; H, 7.41; N, 2.61; S, 6.25.
12. 1; a = 19.542(7) Å. b = 26.97(1) Å. c = 11.695(3) Å; No. of observations (I>2.50s(I)) 4446; R 0.068; Rw 0.074.