Enantioselective palladium catalyzed allylic substitution with new chiral pyridine-phosphine ligands

Tetrahedron Letters

Volumn 38, Issue 34, 1997, Pages 5971-5974

  Brunel, Jean Michel ^a   Constantieux, Thierry ^a   Labande, Agnès ^a   Lubatti, Frédéric ^a   Buono, Gérard ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

MALONIC ACID DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; TEMPERATURE;

EID: 0030738342     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01346-4     Document Type: Article

References (20)

1. For general reviews on palladium catalyzed allylic substìtution, see : (a) Godleski, S. A. in Comprehensive Organic Synthesis, Eds Trost, B. M. ; Fleming, I. ; Pergamon Press, Oxford, 1991, 4, 585.
2. (b) Consiglio, G. ; Waymouth, R. Chem. Rev. 1989, 89, 257-270.
3. (c) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173-1180.
4. (d) Reiser, O. Angew. Chem., Int. Ed. Engl. 1993, 32, 547.
5. (e) Dawson, G. J. ; Williams, J. M. J. ; Coote, S. J. Tetrahedron Asymmetry 1995, 2535-2546 and références therein.
6. (f) Trost, B. M. ; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422.
7. For example : (a) Trost, B. M. ; Organ, M. G. ; O'doherty, G. A. J. Am. Chem. Soc. 1995, 117, 9662-9670.
8. (b) Bolm, C. ; Kaufmann, D. ; Gessler, S. ; Harms, K. J. Organomet. Chem. 1995, 502, 47-52.
9. (c) Seebach, D. ; Devaquet, E. ; Ernst, A. ; Hayakawa, M. ; Kühnle, F. N. M. ; Schweizer, W. B. ; Weber, B. Helv. Chim. Acta 1995, 78, 1636-1650.
10. (a) von Matt, P. ; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-569.
11. (b) Sprinz, J. ; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1773.
12. (c) Dawson, G. J. ; Frost, C. G. ; Williams, J. M. J. ; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149-3150.
13. Akermark, B. ; Hansson, S. ; Krakenberger, B. ; Vitagliano, A. ; Zetterberg, K. Organometallics 1984, 3, 679-682.
14. (b) Akermark, B. ; Krakenberger, B. ; Hansson, S. ; Vitagliano, A. Organometallics 1987, 6, 620-628.
15. (c) Peña-cabrera, E. ; Norrby, P. ; Sjõgren, M. ; Vitagliano, A. ; De Felice, V. ; Oslob, J. ; Ishii, S. ; O'Neill, D. ; Akermark, B. ; Helquist, P. J. Am. Chem. Soc. 1996, 118, 4299-4313.
16. For reviews dealing with the stereocontrol of palladium catalyzed allylic substitution reactions, see : (a) Frost, C. G. ; Williams, J. M. J. Tetrahedron Asymmetry 1992, 3, 1089-1122.
17. (b) Hayashi, T. in Catalytic Asymmetric Synthesis, VCH, Weinheim, Ed. Ojima, I., 1993.
18. Williams, J. M. J. Synlett 1996, 705-710.
19. Chelucci, G. ; Cabras, M. A. ; Botteghi, C. ; Marchetti, M. Tetrahedron Asymmetry 1996, 7, 885-889.
20. 1 was prepared by exchange reaction at 110°C in 20 mL of anhydrous toluene between 163 mg of tris(dimethylamino)phosphine (1 mmole) and 176 mg of (S)-(+)-2-anilinomethylpyrrolidine (1 mmole) for 2 hours, followed by subsequent addition of 136 mg of hydroxyquinoleine (1 mmole). Purification by flash chromatography using ethylacetate as eluent afforded ligand 1 in 72% chemical yield as a white solid stable to air and moisture. Similar procedure was used in order to prepare ligands 2 and 3.