Palladium-catalyzed regio- and stereoselective formate reduction of fluorine-containing allylic mesylates. A new entry for the construction of a tertiary carbon attached with a fluoroalkyl group

Journal of Organic Chemistry

Volumn 71, Issue 9, 2006, Pages 3545-3550

  Konno, Tsutomu ^a   Takehana, Tsuyoshi ^a   Mishima, Makoto ^a   Ishihara, Takashi ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRALITY TRANSFER; MONODENTATE PHOSPHINE; PHOSPHINE LIGAND;

CARBON; CATALYSIS; ESTERS; OPTICAL MATERIALS; PALLADIUM; REDUCTION;

FLUORINE COMPOUNDS;

FLUORINE; FORMIC ACID; MESYLIC ACID; PALLADIUM;

ARTICLE; CATALYSIS; CHIRALITY; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

ALLYL COMPOUNDS; CATALYSIS; FORMATES; HYDROCARBONS, FLUORINATED; MESYLATES; OXIDATION-REDUCTION; PALLADIUM; STEREOISOMERISM;

EID: 33646265553     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0602120     Document Type: Article

References (43)

1. (a) Young, S. D.; Britcher, S. F.; Tran, L. O.; Linda, L. S.; Lumma, W. C.; Lyle, T. A.; Hyff, J. R.; Anderson, P. S.; Olson, D. B.; Carrol, S. S.; Pettibone, Z. D.; Obrien, J. A.; Ball, R. G.; Balani, S. K.; Lin, J. H.; Chen, I. W.; Schleif, W. A.; Sardana, V. V.; Long, W. J.; Brynes, V. W.; Emni, Antimicrob. Agents Chemother. 1995, 39, 2602.
2. (b) Pierce, M. E.; Parsons, R. L., Jr.; Radesca, L. A.; Lo, Y. S.; Silverman, S.; Moore, J. R.; Islam, Q.; Choudhury, A.; Fortunak, J. M. D.; Nguyen, D.; Luo, C.; Mogan, S. J.; Davis, W. P.; Confalone, P. N.; Chen, C.; Tillyer, R. D.; Frey, L.; Tan, L.; Xu, F.; Zhao, D.; Thompson, A. S.; Corley, E. G.; Grabowski, E. J. J.; Reamer, R.; Reider, P. J. J. Org. Chem. 1998, 63, 8536-8543.
3. (a) Mikami, K.; Itoh, Y.; Yamanaka, M. Chem. Rev. 2004, 104, 1-16.
4. (b) Konno, T.; Daitoh, T.; Ishihara, T.; Yamanaka, H. Tetrahedron: Asymmetry 2001, 12, 2743-2748.
5. (c) Lin, P.; Jiang, J. Tetrahedron 2000, 56, 3635-3671.
6. (d) Konno, T.; Ishihara, T.; Yamanaka, H. Tetrahedron Lett. 2000, 41, 8467-8472.
7. (e) Iseki, K. Tetrahedron 1998, 54, 13887-13914.
8. (f) Konno, T.; Umetani, H.; Kitazume, T. J. Org. Chem. 1997, 62, 137-150.
9. (g) Hiraoka, S.; Yamazaki, T.; Kitazume, T. Synlett 1997, 669-670.
10. (h) Konno, T.; Nakano, H.; Kitazume, T. J. Fluorine Chem. 1997, 86, 81-87.
11. (i) Konno, T.; Kitazume, T. Tetrahedron: Asymmetry 1997, 8, 223-230.
12. (j) Yamazaki, T.; Hiraoka, S.; Kitazume, T. Tetrahedron: Asymmetry 1997, 8, 1157-1160.
13. (k) Yamazaki, T.; Umetani, H.; Kitazume, T. Tetrahedron Lett. 1997, 38, 6705-6708.
14. (l) Konno, T.; Yamazaki, T.; Kitazume, T. Tetrahedron 1996, 52, 199-208.
15. (m) Shinohara, N.; Haga, J.; Yamazaki, T.; Kitazume, T.; Nakamura, S. J. Org. Chem. 1995, 60, 4363-4374.
16. (n) Iseki, K.; Nagai, T.; Kobayashi, Y. Tetrahedron: Asymmetry 1994, 5, 961-974.
17. (o) Resnati, G. Tetrahedron 1993, 49, 9385-9445.
18. (p) Yamazaki, T.; Haga, J.; Kitazume, T. Chem. Lett. 1991, 2175-2178.
19. (q) Bravo, P.; Resnati, G. Tetrahedron: Asymmetry 1990, 1, 661-692.
20. (r) Yamazaki, T.; Ishikawa, N.; Iwatsubo, H.; Kitazume, T. J. Chem. Soc., Chem. Commun. 1987, 1340-1342.
21. For the study of the fluorine-containng π-allylpalladium complex, see: (a) Konno, T.; Takehana, T.; Ishihara, T.; Yamanaka, H. Org. Biomol. Chem. 2004, 2, 93-98.
22. (b) Okano, T.; Matsubara, H.; Kusukawa, T.; Fujita, M. J. Organomet. Chem. 2003, 676, 43-46.
23. (c) Konno, T.; Nagata, K.; Ishihara, T.; Yamanaka, H. J. Org. Chem. 2002, 67, 1768-1775.
24. (d) Konno, T.; Ishihara, T.; Yamanaka, H. Tetrahedron Lett. 2000, 41, 8467-8472.
25. (e) Hanzawa, Y.; Ishizawa, S.; Kobayashi, Y. Chem. Pharm. Bull. 1988, 36, 4209-4212.
26. (f) Hanzawa, Y.; Ishizawa, S.; Ito, H.; Kobayashi, Y.; Taguchi, T. J. Chem. Soc., Chem. Commun. 1990, 394-395.
27. For the transition-metal-catalyzed formate reduction, see: (a) Lautens, M.; Paquin, J.-F. Org. Lett. 2003, 5, 3391-3394.
28. (b) Hayashi, T. J. Organomet. Chem. 1999, 576, 195-202.
29. (c) Fuji, K.; Sakurai, M.; Kinoshita, T.; Kawabata, T. Tetrahedron Lett. 1998, 39, 6323-6326.
30. (d) Tsuji, J.; Manda, T. Synthesis 1996, 1-24.
31. (e) Hayashi, T.; Iwamuara, H.; Uozumi, Y.; Matsumoto, Y.; Ozawa, F. Synthesis 1994, 526-532.
32. Kimura, M.; Yamazaki, T.; Kitazume, T.; Kubota, T. Org. Lett. 2004, 6, 4651-4654.
33. (a) Yamazaki, T.; Mizutani, K.; Kitazume, T. J. Org. Chem. 1995, 60, 6046-6056.
34. (b) Mizutani, K.; Yamazaki, T.; Kitazume, T. J. Chem. Soc., Chem. Commun. 1995, 51-52.
35. (a) Konno, T.; Daitoh, T.; Noiri, A.; Chae, J.; Ishihara, T.; Yamanaka, H. Tetrahedron 2005, 61, 9391-9404.
36. (b) Konno, T.; Daitoh, T.; Noiri, A.; Chae, J.; Ishihara, T.; Yamanaka, H. Org. Lett. 2004, 6, 933-936.
37. (c) Wang, J.-J.; Ling, W.; Lu, L. J. Fluorine Chem. 2001, 111, 241-246.
38. (d) Qing, F.-L.; Ying, J.; Zhang, Y. J. Fluorine Chem. 2000, 101, 31-33.
39. (e) Pan, R.-Q.; Liu, X.-X.; Deng, M.-Z. J. Fluorine Chem. 1999, 95, 167-170.
40. (f) Prié, G.; Thibonnet, J.; Abarbri, M.; Duchêne, A.; Parrain, J.-L. Synlett 1998, 839-840.
41. Noyori, R.; Tomino, I.; Tanimoto, Y.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6709-6706.
42. Iseki, K.; Nagai, T.; Kobayashi, Y. Tetrahedron: Asymmetry 1994, 5, 961-974.
43. The similar effect was observed in our previous work. See ref 3a,b.