Asymmetric intermodular heck-type reaction of acyclic alkenes via oxidative palladium(II) catalysis

Organic Letters

Volumn 9, Issue 20, 2007, Pages 3933-3935

  Yoo, Kyung Soo ^b   Park, Chan Pil ^b   Yoon, Cheol Hwan ^b   Sakaguchi, Satoshi ^b   O'Neill, Justin ^b   Jung, Kyung Woon ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^b UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; LIGAND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKENES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PALLADIUM; STEREOISOMERISM;

EID: 35048872146     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701584f     Document Type: Article

References (33)

1. see: (a) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371.
2. (b) Shibasaki, M.; Erasmus, M. V.; Ohshima, T. Heck Reaction. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Chapter 14.
3. (c) Donde, Y.; Overman, L. E. Catalytic Asymmetric Synthesis of All Carbon Quarternary Stereocenters. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 8G.
4. (d) Tietze, L. T.; Ila, H.; Bell, H. P. Chem. Rev. 2004, 104, 3453.
5. (e) Dai, L. X.; Tu, T.; You, S. L.; Deng, W. P.; Hou, X. L. Acc. Chem. Res. 2003, 36, 659.
6. (f) Shibasaki, M.; Vogl, E. M.; Ohshima, T. Adv. Synth. Catal. 2004, 346, 1533.
7. (a) Diederich, F.; Stang, P. J. In Metal-Metal Cross-Coupling Reaction; Wiley-VCH: New York, 1999.
8. (b) Trost, B. M.; Jiang, C. H. Synthesis 2006, 369.
9. (c) Guiry, P. J.; Kiely, D. Curr. Org. Chem. 2004, 8, 781.
10. (d) Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945.
11. (e) Penn, L.; Shpruhman, A.; Gelman, D. J. Org. Chem. 2007, 72, 3875.
12. Alkiyama, K.; Wakabayashi, K.; Mikami, K. Adv. Synth. Catal. 2005, 347, 1569.
13. Dodd, D. W.; Toews, H. E.; Carneiro, F.; Jennings, M. C.; Jones, N. D. Inorg. Chim. Acta 2006, 359, 2850.
14. Yonehara, K.; Mori, K.; Hashizume, T.; Chung, K.-G.; Ohe, K.; Uemura, S. J. Organomet. Chem. 2000, 603, 40.
15. (a) Yoon, C. H.; Yoo, K. S.; Yi, S. W.; Mishra, R. K.; Jung, K. W. Org. Lett. 2004, 6, 4037.
16. (b) Jung, Y. C.; Mishra, R. K.; Yoon, C. H.; Jung, K. W. Org. Lett. 2003, 5, 2231.
17. (c) Parrish, J. P.; Jung, Y. C.; Shin, S. I.; Jung, K. W. J. Org. Chem. 2002, 67, 7127.
18. (a) Yoo, K. S.; Yoon, C. H.; Mishra, R. K.; Jung, Y. C.; Yi, S. W.; Jung, K. W. J. Am. Chem. Soc. 2006, 128, 16384.
19. (b) Enquist, P.-A.; Lindh, J.; Nilsson, P.; Larhed, M. Green Chem. 2006, 8, 338.
20. (c) Andappan, M. M. S.; Nilsson, P.; Larhed, M. Chem. Commun. 2004, 218.
21. (d) von Schenck, H.; Akermark, B.; Svensson, M. J. Am. Chem. Soc. 2003, 125, 3503.
22. Moreno-Manas, M.; Perez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346.
23. (a) Bolm, C.; Weickhardt, K.; Zehnder, M.; Ranff, T. Chem. Ber. 1991, 124, 1173.
24. (b) Brunner, H.; Obermann, U. Chem. Ber. 1989, 122, 499.
25. (c) Sakakura, A.; Kondo, R.; Ishihara, K. Org. Lett. 2005, 7, 1971.
26. For X-ray crystallography analysis data, see the Supporting Information.
27. (a) Shi, M.; Chen, L.-H.; Li, C.-Q. J. Am. Chem. Soc. 2005, 127, 3790.
28. (b) Kawahara, S.; Nakano, A.; Esumi, T.; Iwabuchi, Y.; Hatakeyama, S. Org. Lett. 2003, 5, 3103.
29. (a) For the reaction, see the Supporting Information.
30. (b) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. Angew. Chem., Int. Ed. 2001, 40, 440.
31. (c) Miyamoto, K.; Ohta, H. J. Am. Chem. Soc. 1990, 112, 4077.
32. (d) Miyamoto, K.; Tsuchiya, S.; Ohta, H. J. Fluorine Chem. 1992, 59, 225.
33. (e) Honda, Y.; Ori, A.; Tsuchihashi, G. Bull. Chem. Soc. Jpn. 1987, 60, 1027.