Enantioselective palladium catalyzed allylic substitution with sulfur-containing pyridine ligands

Tetrahedron Asymmetry

Volumn 7, Issue 4, 1996, Pages 965-966

  Chelucci, Giorgio ^a   Cabras, M Antonietta ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; PYRIDINE DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; DRUG PURITY; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029965916     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00092-4     Document Type: Article

References (18)

1. Reiser, O. Angew. Chem., 1993, 105, 576; Angew. Chem. Int. Ed. Engl., 1993, 32, 547; Hayashi, T., in Catalytic Asymmetric Synthesis, Ed. Ojima, VCH, Weinheim, 1993; Frost, C.G., Howarth, J., Williams, J.M.J. Tetrahedron: Asymmetry, 1992, 3, 1089. Dawson, G.J., Williams, J.M.J., Coote, S.J. Tetrahedron: Asymmetry, 1995, 2535, and references therein.
2. Reiser, O. Angew. Chem., 1993, 105, 576; Angew. Chem. Int. Ed. Engl., 1993, 32, 547; Hayashi, T., in Catalytic Asymmetric Synthesis, Ed. Ojima, VCH, Weinheim, 1993; Frost, C.G., Howarth, J., Williams, J.M.J. Tetrahedron: Asymmetry, 1992, 3, 1089. Dawson, G.J., Williams, J.M.J., Coote, S.J. Tetrahedron: Asymmetry, 1995, 2535, and references therein.
3. Reiser, O. Angew. Chem., 1993, 105, 576; Angew. Chem. Int. Ed. Engl., 1993, 32, 547; Hayashi, T., in Catalytic Asymmetric Synthesis, Ed. Ojima, VCH, Weinheim, 1993; Frost, C.G., Howarth, J., Williams, J.M.J. Tetrahedron: Asymmetry, 1992, 3, 1089. Dawson, G.J., Williams, J.M.J., Coote, S.J. Tetrahedron: Asymmetry, 1995, 2535, and references therein.
4. Reiser, O. Angew. Chem., 1993, 105, 576; Angew. Chem. Int. Ed. Engl., 1993, 32, 547; Hayashi, T., in Catalytic Asymmetric Synthesis, Ed. Ojima, VCH, Weinheim, 1993; Frost, C.G., Howarth, J., Williams, J.M.J. Tetrahedron: Asymmetry, 1992, 3, 1089. Dawson, G.J., Williams, J.M.J., Coote, S.J. Tetrahedron: Asymmetry, 1995, 2535, and references therein.
5. Reiser, O. Angew. Chem., 1993, 105, 576; Angew. Chem. Int. Ed. Engl., 1993, 32, 547; Hayashi, T., in Catalytic Asymmetric Synthesis, Ed. Ojima, VCH, Weinheim, 1993; Frost, C.G., Howarth, J., Williams, J.M.J. Tetrahedron: Asymmetry, 1992, 3, 1089. Dawson, G.J., Williams, J.M.J., Coote, S.J. Tetrahedron: Asymmetry, 1995, 2535, and references therein.
6. Allen, J.V., Coote, S.J., Dawson, G.J., Frost, C.G., Martin, C.J., Williams, J.M.J., J. Chem. Soc., Perkin Trans.1, 1994, 2065. Sprinz, J., Kiefer, M., Helmchen, G., Reggelin, M., Huttner, G., Walter, O., Zsolnai, L. Tetrahedron Letters, 1994, 1523.
7. Allen, J.V., Coote, S.J., Dawson, G.J., Frost, C.G., Martin, C.J., Williams, J.M.J., J. Chem. Soc., Perkin Trans.1, 1994, 2065. Sprinz, J., Kiefer, M., Helmchen, G., Reggelin, M., Huttner, G., Walter, O., Zsolnai, L. Tetrahedron Letters, 1994, 1523.
8. Basoli, C. Botteghi, C., Cabras, M.A., Chelucci, G., Marchetti, M. J. Organometal. Chem., 1995, 488, C20-C22; Chelucci, G., Cabras, M.A, Saba, A. J. Mol. Catalysis, 1995, 95, L7-L10; Chelucci, G., Cabras, M.A., Botteghi, C., Marchetti, M. Tetrahedron: Asymmetry, 1994, 5, 299.
9. Basoli, C. Botteghi, C., Cabras, M.A., Chelucci, G., Marchetti, M. J. Organometal. Chem., 1995, 488, C20-C22; Chelucci, G., Cabras, M.A, Saba, A. J. Mol. Catalysis, 1995, 95, L7-L10; Chelucci, G., Cabras, M.A., Botteghi, C., Marchetti, M. Tetrahedron: Asymmetry, 1994, 5, 299.
10. Basoli, C. Botteghi, C., Cabras, M.A., Chelucci, G., Marchetti, M. J. Organometal. Chem., 1995, 488, C20-C22; Chelucci, G., Cabras, M.A, Saba, A. J. Mol. Catalysis, 1995, 95, L7-L10; Chelucci, G., Cabras, M.A., Botteghi, C., Marchetti, M. Tetrahedron: Asymmetry, 1994, 5, 299.
11. For a review: Chelucci, G. Gazz.Chim. Ital. 1992, 122, 89.
12. During the drafting of this paper an analogue strategy in the synthesis of 2-(1-hydroxyalkyl)pyridines was reported: Collomb, P., von Zelewsky , A. Tetrahedron: Asymmetry, 1995, 2903.
13. Birch, A.J., Raverty, W.D., Stephenfon, G.R., Organometallics, 1984, 3, 1075.
14. D -21 (neat), 92 % ee} was purchased from Aldrich Chemical Co. Ltd.
15. King, L.C. J. Am. Chem.Soc., 1944, 66, 894.
16. Krohnke, F. Synthesis, 1976, 1.
17. 3, 300 MHz) δ: 8.01 (d, 2H), 7.84 (d, 2H), 7.52-7.19 (m, 8H), 4.83 (s, 1H), 2.74 (m, 3H), 1.41 (s, 3H), 1.39 (overlapping, 1H), 0.88 (s, 3H).
18. Trost, B.M., Murphy, D.J. Organometallics, 1985, 4, 1143.