Sulfoxides as stereochemical controllers in intermolecular Heck reactions

Chemistry - A European Journal

Volumn 7, Issue 18, 2001, Pages 3890-3900

  Díaz Buezo, Nuria ^a   De La Rosa, Juan Carlos ^a   Priego, Julián ^a   Alonso, Inés ^a   Carretero, Juan Carlos ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Asymmetric synthesis; Cyclopentenes; Dihydrofurans; Heck reaction; Sulfoxides

Indexed keywords

CATALYSTS; ISOMERS; PALLADIUM COMPOUNDS; SUBSTITUTION REACTIONS;

INDUCTIONS;

SULFUR COMPOUNDS;

CYCLOPENTENE DERIVATIVE; DIHYDROFURAN; FURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHIRALITY; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0035903604     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010917)7:18<3890::AID-CHEM3890>3.0.CO;2-Y     Document Type: Article

References (54)

1. Recent reviews: a) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009;
2. b) S. Bräse, A. de Meijere in Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapt. 3;
3. c) S. E. Gibson, R. J. Middleton, Contemp. Org. Synth. 1996, 3, 447;
4. d) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2;
5. e) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473;
6. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379.
7. For reviews on the asymmetric Heck reaction, see: a) M. Shibasaki, E. M. Vogl, J. Organomet. Chem. 1999, 576, 1;
8. b) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371;
9. c) P. J. Guiry, A. J. Hennessy, J. P. Cahill, Top. Catal. 1997, 4, 311.
10. For some recent references, see: a) D. Flubacher, G. Helmchen, Tetrahedron Lett. 1999, 40, 3867;
11. b) J. C. Namyslo, D. E. Kaufmann, Synlett 1999, 804;
12. c) F. Miyazaki, K. Uotsu, M. Shibasaki, Tetrahedron 1998, 54, 13073;
13. d) A. Kojima, T. Takemoto, M. Sodeoka, M. Shibasaki, Synthesis 1998, 581.
14. R. Grigg, M. J. R. Dorrty, J. F. Malone, Tetrahedron Lett. 1990, 31, 3075.
15. a) J. L. García Ruano, B. Cid de la Plata, Top. Curr. Chem. 1999, 204, 1;
16. b) M. C. Aversa, A. Barattucci, P. Bonaccorsi, P. Gianneto, Tetrahedron: Asymmetry 1997, 8, 1339;
17. c) C. Carreño, Chem. Rev. 1995, 95, 1717.
18. For the use of sulfoxides as chiral auxiliaries in Pauson-Khand reactions, see: J. Adrio, J. C. Carretero, J. Am. Chem. Soc. 1999, 121, 7411.
19. Previous communications: a) J. C. de la Rosa, N. Díaz Buezo, J. C. Carretero, Tetrahedron Lett. 2000, 41, 4107;
20. b) N. Díaz Buezo, I. Alonso, J. C. Carretero, J. Am. Chem. Soc. 1998, 120, 7129.
21. For intramolecular processes, see: c) N. Díaz Buezo, O. García Mancheño, J. C. Carretero, Org. Lett. 2000, 2, 1451.
22. S. Jain, K. Shukla, A. Mukhopadhyay, S. N. Suryawanshi, D. S. Bhakuni, Synth. Commun. 1990, 20, 1315.
23. J. Priego, J. C. Carretero, Synlett 1999, 1603.
24. Incomplete reactions were always observed with an equimolecular amount of iodobenzene. On the other hand, other electrophiles, such as bromobenzene and phenyltriflate, were also used in these Heck reactions. However, these electrophiles were much less reactive than iodobenzene; they gave low conversions and therefore very poor yields of Heck products.
25. a) B. C. Soderberg in Comprehensive Organometallic Chemistry II, Vol. 3 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, p. 241-297.
26. See also: b) S. O. Hillers, O. Reiser, Synlett 1995, 153.
27. Dihydrofurans and cyclopentenes are very prone to undergo double-bond isomerization in Heck reactions. For some asymmetric Heck reactions of dihydrofurans and cyclopentenes, see, for instance: a) S. R. Gilbertson, Z. Fu, D. Xie, Tetrahedron Lett. 2001, 42, 365;
28. b) A. J. Hennessy, Y. M. Malone, P. J. Guiry, Tetrahedron Lett. 2000, 41, 2261;
29. c) Y. Hashimoto, Y. Horie, M. Hayashi, K. Saigo, Tetrahedron: Asymmetry 2000, 11, 2205;
30. d) C. G. Hartung, K. Köhler, M. Beller, Org. Lett. 1999, 1, 709;
31. e) O. Loiseleur, M. Hayashi, N. Schmees, A. Pfaltz, Synthesis 1997, 1338;
32. f) K. K. Hii, T. D. W. Claridge, J. M. Brown, Angew. Chem. 1997, 109, 1033;
33. Angew. Chem. Int. Ed. Engl. 1997, 36, 984;
34. g) S. Hillers, S. Sartori, O. Reiser, J. Am. Chem. Soc. 1996, 118, 2087;
35. h) O. Loiseleur, P. Meier, P. A. Pfaltz, Angew. Chem. 1996, 108, 218;
36. Angew. Chem. Int. Ed. Engl. 1996, 35, 200.
37. R. Lett, A. Marquet, Tetrahedron 1974, 30, 3379.
38. For Pd-N coordinated complexes in Heck reactions of acyclic nitrogen-containing vinyl ethers, see: a) M. Larhed, C. Andersson, A. Hallberg, Tetrahedron 1994, 50, 285;
39. b) C. Andersson, J. Larsson, A. Hallberg, J. Org. Chem. 1990, 55, 5757;
40. c) K. Olofsson, H. Sahlin, M. Larhed, A. Hallberg, J. Org. Chem. 2001, 66, 544.
41. For conformational studies in α,β-unsaturated sulfoxides, see: a) L. F. Tietze, A. Schuffenhauer, P. R. Schreiner, J. Am. Chem. Soc. 1998, 120, 7952;
42. b) I. Arai, H. Takayama, T. Koizumi, Tetrahedron Lett. 1987, 28, 3689.
43. Taking into account that the best diastereoselectivities in the Heck arylations of alkenes 4 and 8 were obtained in the presence of bidentate phosphines, the participation of pentacoordinate palladium intermediates, instead of the tetracoordinate complex D, cannot be ruled out. For asymmetric Heck reactions that involve five-coordinate palladium intermediates, see: a) A. Ashimori, B. Bachand, L. E. Overman, D. J. Poon, J. Am. Chem. Soc. 1998, 120, 6477;
44. b) A. Ashimori, B. Bachand, M. A. Calter, S. P. Govek, L. E. Overman, D. J. Poon, J. Am. Chem. Soc. 1998, 120, 6488.
45. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication nos. CCDC-160841 ((±)-24) and CCDC-149387 ((3R, SR)-25). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
46. J.-M. Brunel, P. Diter, M. Duetsch, H. B. Kagan, J. Org. Chem. 1995, 60, 8086.
47. F. A., Davis, R. T. Reddy, W. Han, P. J. Carroll, J. Am. Chem. Soc. 1992, 114, 1428.
48. (S)-30 was prepared following the DAG methodology: I. Fernández, N. Khiar, J. M. Llera, F. Alcudia, J. Org. Chem. 1992, 57, 6789.
49. F. Rebiere, O. Samuel, L. Ricard, H. B. Kagan, J. Org. Chem. 1991, 56, 5991.
50. R. A. Holton, D. J. Crouse, A. D. Williams, R. M. Kennedy, J. Org. Chem. 1987, 52, 2317.
51. A. D. Rodríguez, O. M. Cóbar, O. L. Padilla, J. Nat. Prod. 1997, 60, 915.
52. Unlike the case of the sulfinyldihydrofurans, the reaction of sulfinylcyclopentane 14 with activated zinc gave exclusively the corresponding thioether instead of the C-S cleavage product.
53. M. Julia, J. L. Fabre, Tetrahedron Lett. 1983, 24, 4311.
54. G. M. Sheldrick, SHELX-97, University of Göttingen, Göttingen (Germany), 1998.