A comparison of palladium complexes of BINAP and diphenylphosphinooxazoline ligands in the catalytic asymmetric synthesis of cis-decalins

Tetrahedron Letters

Volumn 44, Issue 39, 2003, Pages 7377-7380

  Kiely, Denis ^a   Guiry, Patrick J ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

1 METHYLPYRROLE; BASE; DECALIN DERIVATIVE; DIPHENYLPHOSPHINOFERROCENYLOXAZOLINE; LEUCINE; LIGAND; N,N DIMETHYLACETAMIDE; OXAZOLINE DERIVATIVE; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE; POTASSIUM CARBONATE; SOLVENT; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; COMPARATIVE STUDY; COMPLEX FORMATION; CYCLIZATION; DERIVATIZATION; ENANTIOSELECTIVITY; MOLECULE; SYNTHESIS;

EID: 0042381650     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01877-X     Document Type: Article

References (24)

1. General Heck reaction reviews, see: (a) De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379; (b) Heck, R. F. Acc. Chem. Res. 1978, 12, 146; (c) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2; (d) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009; (e) Jeffery, T. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; Jai Press: Greenwich, CT, 1996; Vol. 5.
2. General Heck reaction reviews, see: (a) De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379; (b) Heck, R. F. Acc. Chem. Res. 1978, 12, 146; (c) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2; (d) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009; (e) Jeffery, T. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; Jai Press: Greenwich, CT, 1996; Vol. 5.
3. General Heck reaction reviews, see: (a) De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379; (b) Heck, R. F. Acc. Chem. Res. 1978, 12, 146; (c) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2; (d) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009; (e) Jeffery, T. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; Jai Press: Greenwich, CT, 1996; Vol. 5.
4. General Heck reaction reviews, see: (a) De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379; (b) Heck, R. F. Acc. Chem. Res. 1978, 12, 146; (c) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2; (d) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009; (e) Jeffery, T. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; Jai Press: Greenwich, CT, 1996; Vol. 5.
5. General Heck reaction reviews, see: (a) De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379; (b) Heck, R. F. Acc. Chem. Res. 1978, 12, 146; (c) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2; (d) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009; (e) Jeffery, T. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; Jai Press: Greenwich, CT, 1996; Vol. 5.
6. For a review on the Heck reaction in natural product synthesis, see: Link, J. T.; Overman, L. E. In Metal Catalysed Cross Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 3.
7. For asymmetric Heck reviews, see: (a) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371; (b) Donde, Y.; Overman, L. E. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH, 2000; pp. 675-695; (c) Guiry, P. J.; Hennessy, A. J.; Cahill, J. P. Top. Catal. 1997, 4, 311.
8. For asymmetric Heck reviews, see: (a) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371; (b) Donde, Y.; Overman, L. E. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH, 2000; pp. 675-695; (c) Guiry, P. J.; Hennessy, A. J.; Cahill, J. P. Top. Catal. 1997, 4, 311.
9. For asymmetric Heck reviews, see: (a) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371; (b) Donde, Y.; Overman, L. E. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH, 2000; pp. 675-695; (c) Guiry, P. J.; Hennessy, A. J.; Cahill, J. P. Top. Catal. 1997, 4, 311.
10. Sato Y., Sodeoka M., Shibasaki M. J. Org. Chem. 54:1989;4738.
11. Carpenter N.E., Kucera D.J., Overman L.E. J. Org. Chem. 54:1989;5846.
12. Sato Y., Watanabe S., Shibasaki M. Tetrahedron Lett. 33:1992;2589.
13. Ripa L., Hallberg A. J. Org. Chem. 62:1997;595.
14. Loiseleur O., Meier P., Pfaltz A. Angew. Chem., Int. Ed. Engl. 35:1996;200.
15. Loiseleur O., Hayashi M., Schmees N., Pfaltz A. Synthesis. 11:1997;1338.
16. Hennessy A.J., Malone Y.M., Guiry P.J. Tetrahedron Lett. 40:1999;9163.
17. Hennessy A.J., Malone Y.M., Guiry P.J. Tetrahedron Lett. 41:2000;2261.
18. Hennessy A.J., Connolly D.J., Malone Y.M., Guiry P.J. Tetrahedron Lett. 41:2000;7757.
19. Kilroy, T. G.; Hennessy, A. J.; Connolly, D. J.; Malone, Y. M.; Farrell, A.; Guiry, P. J. J. Mol. Cat. A 2003, 196/1-2, 65.
20. Kiely D., Guiry P.J. Tetrahedron Lett. 43:2002;9545.
21. Busacca C.A., Grossbach D., So R.C., O'Brien E.M., Spinelli E.M. Org. Lett. 5:2003;595.
22. Ohrai K., Kondo K., Sodeoka M., Shibasaki M. J. Am. Chem. Soc. 116:1994;11737.
23. 3 (6.7 mg, 0.0075 mmol) and toluene (0.5 mL). The purple suspension thus obtained was stirred for 1 h under a nitrogen atmosphere and had then become an orange solution. Methyl 1-[4-[(trifluoromethyl)sulfonyl]oxy]-3(Z)-butenyl-2, 5-cyclohexadiene-1-carboxylate (50 mg, 0.15 mmol) was then added in toluene (1. 0 mL) followed by potassium carbonate (41.4 mg, 0.3 mmol). The reaction mixture was degassed by the freeze-thaw-pump method (×3), sealed and heated at 60°C for 72 h. The reaction mixture was allowed to cool to room temperature, then diluted with ether (5 mL), washed with brine (5 mL), dried over magnesium sulfate and concentrated in vacuo. The crude residue was further purified by column chromatography on silica gel (10:1 hexane/ether) to give methyl-3,8a-dihydro-4a-4H-naphthalenecarboxylate as a colourless oil (14.0 mg, 51%).
24. 1′).