Enantioselective palladium-catalyzed addition of 1,3-dicarbonyl compounds to an allene derivative

Chemistry - A European Journal

Volumn 11, Issue 23, 2005, Pages 7075-7082

  Trost, Barry M ^a   Simas, Alessandro B C ^a   Plietker, Bernd ^a   Jäkel, Christoph ^a   Xie, Jia ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

Alkylation; Allylic compounds; Asymmetric catalysis; Palladium; Proelectrophiles; Pronucleophiles

Indexed keywords

ALLYLIC COMPOUNDS; ASYMMETRIC CATALYSIS; PROELECTROPHILES; PRONUCLEOPHILES;

ACETIC ACID; ACIDITY; ADDITION REACTIONS; ALKYLATION; CATALYSIS; DERIVATIVES; OPTIMIZATION; PALLADIUM; PH EFFECTS;

ORGANIC COMPOUNDS;

ALKADIENE; ALLENE; PALLADIUM;

CATALYSIS; CHEMISTRY; CONFERENCE PAPER; ELECTROSPRAY MASS SPECTROMETRY; STEREOISOMERISM;

ALKADIENES; CATALYSIS; PALLADIUM; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM;

EID: 28044446114     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200500826     Document Type: Conference Paper

References (48)

1. a) D. A. Spiegel, J. T. Njardarson, I. M. McDonald, J. L. Wood, Chem. Rev. 2003, 105, 2691-2727;
2. b) S. J. Mickel, D. Niederer, R. Daeffler, A. Osmani, E. Kuesters, E. Schmid, K. Schaer, R. Gamboni, W. Chen, E. Loeser, F. R. Kinder Jr., K. Konigsberger, K. Prasad, T. M. Ramsey, O. Repic, R.-M. Wang, Org. Process Res. Dev. 2004, 5, 122-130 and preceding papers;
3. c) C. H. Heathcock, M. McLaughlin, J. Medina, J. L. Hubbs, G. A. Wallace, R. Scott, M. M. Claffey, C. J. Hayes, G. R. Ott, J. Am. Chem. Soc. 2003, 125, 12844-12849;
4. d) J. L. Hubbs, C. H. Heathcock, J. Am. Chem. Soc. 2003, 125, 12836-12843.
5. a) S. L. Schreiber, Chem. Eng. News 2003, 81(9), 51-61;
6. b) See also: S. Borman, Chem. Eng. News 2004, 82(9), 32-40.
7. B. M. Trost, Pure Appl. Chem. 1979, 51, 787-800.
8. B. M. Trost, Science 1991, 254, 1471-1477.
9. R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 90;
10. Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69.
11. a) B. M. Trost, Acc. Chem. Res. 1996, 29, 355-364;
12. b) B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422.
13. a) R. Noyori, M. Kitamura, T. Ohkuma, Proc. Natl. Acad. Sci. USA 2004, 101, 5356-5362;
14. b) B. M. Trost, Proc. Natl. Acad. Sci. USA 2004, 101, 5348-5355;
15. c) Comprehensive Asymmetric Catalysis, Vols. I-III (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Spring, Berlin, 2000.
16. T. Hudlicky, Chem. Rev. 1996, 96, 3-30.
17. a) B. M. Trost, Angew. Chem. 1995, 107, 285;
18. Angew. Chem. Int. Ed. Engl. 1995, 34, 259-281;
19. b) B. M. Trost, Acc. Chem. Res. 2002, 35, 695-705.
20. B. M. Trost, V. J. Gerusz, J. Am. Chem. Soc. 1995, 117, 5156-5157.
21. Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019-6020.
22. B. M. Trost, P.-Y. Michellys, V. J. Gerusz, Angew. Chem. 1997, 109, 1837-1839;
23. Angew. Chem. Int. Ed. Engl. 1997, 36, 1750-1753.
24. B. M. Trost, C. Jäkel, B. Plietker, J. Am. Chem. Soc. 2003, 125, 4438-4439.
25. a) B. M. Trost, J. Org. Chem. 2004, 69, 5813-5837;
26. b) B. M. Trost. M. L. Crawley, Chem. Rev. 2003, 103, 2921-2943.
27. Y. Yamamoto, M. Al-Masum, Synlett 1995, 969-970.
28. a) I. J. S. Fairlamb, G. C. Lloyd-Jones, Chem. Commun. 2000, 2447-2448;
29. b) B. M. Trost, J.-P. Surivet, J. Am. Chem. Soc. 2000, 122, 6291-6292.
30. a) M. P. T. Sjogren, S. Hansson, B. Åkermark, A. Vitagliano, Organometallics 1994, 13, 1963;
31. b) U. Burckhardt, M. Baumann, A. Togni, Tetrahedron: Asymmetry 1997, 8, 155;
32. c) B. M. Trost, R. C. Bunt, J. Am. Chem. Soc. 1998, 120, 70-79;
33. d) B. M. Trost, G. M. Schroeder, J. Org. Chem. 2000, 65, 1569-1573.
34. B. M. Trost, F. D. Toste, J. Am. Chem. Soc. 1999, 121, 4545-4554.
35. Y. I. M. Nilsson, P. G. Andersson, J. E. Bäckvall, J. Am. Chem. Soc. 1993, 115, 6609-6613;
36. N. Vicart, J. Gore, B. Cazes, Synlett 1996, 850-852.
37. V. V. Grushin, Chem. Rev. 1996, 96, 2011-2033.
38. a) C. Amatore, A. Jutand, G. Meyer, I. Carelli, I. Chiarotto, Eur. J. Inorg. Chem. 2000, 1855-1859; for recent findings on the importance of palladium hydride species, see:
39. b) I. D. Hills, G. C. Fu, J. Am. Chem. Soc. 2004, 126, 13178-13179.
40. a) F. P. J. T. Rutjes, T. M. Kooistra, H. Hiemstra, H. E. Schoemaker, Synlett 1998, 192-194;
41. b) H. Ovaa, M. A. Leeuwenburgh, G. A. van de Marcel, J. H. van Boom, Tetrahedron Lett. 1998, 39, 3025-3028.
42. F. Bordwell, Acc. Chem. Res. 1988, 21, 456-463.
43. S. K. Latypov, J. M. Seco, E. Quiñoá, R. Riguera, J. Org. Chem. 1996, 61, 8569-8577.
44. G. Giambastiani, G. Poli, J. Org. Chem. 1998, 63, 9608-9609.
45. a) B. M. Trost, F. D. Toste, J. Am. Chem. Soc. 1998, 120, 9074-9075;
46. b) B. M. Trost, M. J. Krische, R Radinov, G. Zanoni, J. Am. Chem. Soc. 1996, 118, 6297-6298.
47. For cases in which π-facial discrimination does not seem to operate efficiently, see: a) reference [18];
48. b) B. M. Trost, H. C. Shen, L. Dong, J. -P. Surivet, C. Sylvain, J. Am. Chem. Soc. 2004, 126, 11966-11983.