Dynamic kinetic asymmetric allylic alkylations of allenes

Journal of the American Chemical Society

Volumn 127, Issue 41, 2005, Pages 14186-14187

  Trost, Barry M ^a   Fandrick, Daniel R ^a   Dinh, Diana C ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; PALLADIUM;

ALKYLATION; ARTICLE; ATOMIC PARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STRUCTURE ANALYSIS;

ALKADIENES; ALKENES; ALKYLATION; CATALYSIS; KINETICS; LIGANDS; MOLECULAR CONFORMATION; PALLADIUM; STEREOISOMERISM;

EID: 26844518922     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0543705     Document Type: Article

References (33)

1. (a) Trost, B. M. Science 1991, 254, 1471-1477.
2. (b) Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705.
3. (a) Hoffmann-Roder, A.; Krause, N. Angew. Chem., Int. Ed. 2002, 41, 2933-2935.
4. (b) Hoffmann-Roder, A.; Krause, N. Angew. Chem., Int. Ed. 2004, 43, 1196-1216.
5. Modern Allene Chemistry; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH: Weinhein, Germany, 2004.
6. (d) Marshall, J. A.; Mulheam, J. J. Org. Lett. 2005, 7, 1593-1596.
7. (a) Brummond, K. M.; Kerekes, A. D.; Wan, H. J. Org. Chem. 2002, 67, 5156-5163.
8. (b) Ma, S. Chem. Rev. 2005 105, 2829-2872.
9. Myers, A. G.; Zheng, B. J. Am. Chem. Soc. 1996, 118, 4492-4493.
10. (a) Mikami, K.; Yoshida, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 858-860.
11. (b) Han, J. W.; Tokunaga, N.; Hayashi, T. J. Am. Chem. Soc. 2001, 123, 12915-12916.
12. Imada, Y.; Ueno, K.; Kutsuwa, K.; Murahashi, S. Chem. Lett. 2002, 140-141.
13. (a) Ogasawara, M.; Ikeda, H.; Hayashi, T. Angew. Chem., Int. Ed. 2000, 39, 1042-1044.
14. (b) Ogasawara, M.; Ikeda, H.; Nagano, T.; Hayashi, T. J. Am. Chem. Soc. 2001, 123, 2089-2090.
15. (c) Ogasawara, M.; Ueyama, K.; Nagano, T.; Mizuhata, Y.; Hayashi, T. Org. Lett. 2003, 5, 217-219.
16. (d) Ogasawara, M.; Nagano, T.; Hayashi, T. J. Org. Chem. 2005, 70, 5764-5767.
17. (a) Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1-14.
18. (b) Trost, B. M. Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
19. (c) Trost, B. M.; Fandrick, D. R. J. Am. Chem. Soc. 2003, 125, 11836-11837.
20. (d) Trost, B. M. J. Org. Chem. 2004, 69, 5813-5837.
21. (e) Trost, B. M.; Fandrick, D. R. Org. Lett. 2005, 7, 823-826.
22. Conditions of: Campos, K. R.; Journet, M.; Lee, S.; Grabowski, E. J. J.; Tillyer, R. D. J. Org. Chem. 2005, 70, 268-274.
23. (a) Lowe, G. J. Chem. Soc., Chem. Commun. 1965, 411-413.
24. (b) Brewster, J. H. Top. Stereochem. 1967, 2, 1-72.
25. Trost, B. M. Acc. Chem. Res. 1996, 29, 355-364.
26. LiHMDS (lithium bis(trimethylsilyl)amide) was employed as the standard base due to the increased shelf life over LDA.
27. Enantiomers not separable by Chiralcel OB-H, OC, OD-H, OJ, and Chiralpak AD and AS HPLC.
28. For Diels-Alder reactions of allenes, see: (a) Gibbs, R. A.; Okamura, W. H. J. Am. Chem. Soc. 1988, 110, 4062-4063.
29. (b) Hayakawa, K.; Nagatsugi F.; Kanematsu, K. J. Org. Chem. 1988, 53, 860-863.
30. (c) Bull, J. R.; Gordon, R.; Hunter, R. J. Chem. Soc., Perkin Trans. 1 2000, 3129-3139.
31. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.
32. (a) Paik, S.-J.; Son, S. U.; Chung, Y. K. Org. Lett. 1999, 1, 2045-2047.
33. (b) Wender, P. A.; Williams, T. J. Angew. Chem., Int. Ed. 2002, 41, 4550-4553.