An efficient and general route to reduced polypropionates via Zr-catalyzed asymmetric C-C bond formation

Proceedings of the National Academy of Sciences of the United States of America

Volumn 101, Issue 16, 2004, Pages 5782-5787

  Negishi, Ei Ichi ^a   Tan, Ze ^a   Liang, Bo ^a   Novak, Tibor ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKANE DERIVATIVE; ALKANOL; ALUMINUM DERIVATIVE; BUTANOL; CARBON; HEXANOL; METHYL GROUP; PENTANOL; PROPANE; PROPIONIC ACID DERIVATIVE; ZIRCONIUM;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; COMMERCIAL PHENOMENA; ENANTIOMER; IODINATION; MATERIAL STATE; OXIDATION; PRIORITY JOURNAL; STEREOISOMERISM; SYNTHESIS;

CARBON; CATALYSIS; MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION-REDUCTION; PROPIONATES; STEREOISOMERISM; ZIRCONIUM;

EID: 1942533588     PISSN: 00278424     EISSN: None     Source Type: Journal    
DOI: 10.1073/pnas.0307514101     Document Type: Article

References (49)

1. Janiak, C. (1998) in Metallocenes, ed. Togni, A. (Wiley-VCH, Weinheim, Germany), pp. 547-628.
2. Stoermer, D., Caron, S. & Heathcock, C. H. (1996) J. Org. Chem. 61, 9115-9125.
3. Kohno, J., Nishio, M., Sakurai, M., Kawano, K., Hiramatsu, H., Kameda, N., Kishi, N., Yamashita, T., Okuda, T. & Komatsubara, S. (1999) Tetrahedron 55, 7771-7786.
4. Andersen, A., Cordes, H.-G., Herwig, J., Kaminsky, W., Merch, A., Mottweiler, R., Rein, J., Sinn, H. & Vollmer, H.-J. (1976) Angew. Chem. Int. Ed. 15, 630-632.
5. Wang, Y. F., Chen, C. S., Girdaukas, G. & Sih, C. J. (1984) J. Am. Chem. Soc. 106, 3695-3696.
6. Hoye, T. R. & Tennakoon, M. A. (2000) Org. Lett. 2, 1481-1483.
7. Fujita, K. & Mori, K. (2001) Eur. J. Org. Chem. 493-502.
8. Hanessian, S., Cooke, N. G., DeHoff, B. & Sakito, Y. (1990) J. Am. Chem. Soc. 112, 5276-5290.
9. Evans, D. A., Dow, R. L., Shih, T. L., Takacs, J. M. & Zahler, R. (1990) J. Am. Chem. Soc. 112, 5290-5313.
10. Abiko, A. & Masamune, S. (1996) Tetrahedron Lett. 37, 1081-1084.
11. Myers, A. G., Yang, B. H., Chen, H., McKinstry, L., Kopecky, D. J. & Gleason, J. L. (1997) J. Am. Chem. Soc. 119, 6496-6511.
12. Myers, A. G., Yang, B. H., Chen, H. & Kopecky, D. J. (1997) Synlett 457-459.
13. Birkbeck, A. A. & Enders, D. (1998) Tetrahedron Lett. 39, 7823-7826.
14. Nicolas, E., Russell, K. C. & Hruby, V. J. (1993) J. Org. Chem. 58, 766-770.
15. Williams, D. R. & Turske, R. A. (2000) Org. Lett. 2, 3217-3220.
16. Ghosh, A. K. & Liu, C. (2001) Org. Lett. 3, 635-638.
17. Charette, A. B. & Juteau, H. (1994) J. Am. Chem. Soc. 116, 2651-2652.
18. Charette, A. B. & Naud, J. (1998) Tetrahedron Lett. 39, 7259-7262.
19. Calter, M. A., Liao, W. & Struss, J. A. (2001) J. Org. Chem. 66, 7500-7504.
20. Calter, M. A. & Liao, W. (2002) J. Am. Chem. Soc. 124, 13127-13129.
21. Takaya, H., Ohta, T., Sayo, N., Kumobayashi, H., Akutagawa, S., Inoue, S., Kasahara, I. & Noyori, R. (1987) J. Am. Chem. Soc. 109, 1596-1597.
22. Kondakov, D. Y. & Negishi, E. (1995) J. Am. Chem. Soc. 117, 10771-10772.
23. Kondakov, D. Y. & Negishi, E. (1996) J. Am. Chem. Soc. 118, 1577-1578.
24. Van Horn, D. E. & Negishi, E. (1978) J. Am. Chem. Soc. 100, 2252-2254.
25. Erker, G., Aulback, M., Knickmeier, M., Wingbermüdhle, D., Krüger, C., Nolte, M. & Werner, S. (1993) J. Am. Chem. Soc. 115, 4590-4601.
26. Grubbs, R. H. & Coates, G. W. (1996) Acc. Chem. Res. 29, 85-93.
27. Huo, S. & Negishi, E. (2001) Org. Lett. 3, 3253-3256.
28. Wipf, P. & Ribe, S. (2000) Org. Lett. 2, 1713-1716.
29. Huo, S., Shi, J. & Negishi, E. (2002) Angew. Chem. Int. Ed. 41, 2141-2143.
30. Shaughnessy, K. H. & Waymouth, R. M. (1998) Organometallics 17, 5728-5745.
31. Negishi, E., Van Horn, D. E. & Yoshida, T. (1985) J. Am. Chem. Soc. 107, 6639-6647.
32. Takahashi, T., Seki, T., Nitto, Y., Saburi, M., Rousset, C. J. & Negishi, E. (1991) J. Am. Chem. Soc. 113, 6266-6268.
33. Negishi, E., Kondakov, D. Y., Choueiry, D., Kasai, K. & Takahashi, T. (1996) J. Am. Chem. Soc. 118, 9577-9588.
34. Negishi, E. & Kondakov, D. Y. (1996) Chem. Soc. Rev. 26, 417-426.
35. Negishi, E. (1999) Chem. Eur. J. 5, 411-420.
36. Negishi, E. & Huo, S. (2002) in Titanium and Zirconium in Organic Synthesis ed. Marek, I. (Wiley-VCH, Weinheim, Germany), pp. 1-49.
37. Morken, J. P., Didiuk, M. T. & Hoveyda, A. H. (1993) J. Am. Chem. Soc. 115, 6997-6998.
38. Hoveyda, A. H. & Morken, J. P. (1996) Angew. Chem. Int. Ed. 35, 1263-1284.
39. Bell, L., Whitby, R. J., Jones, R. V. H. & Standen, M. C. H. (1996) Tetrahedron Lett. 37, 7139-7142.
40. Yamanaka, Y., Hyakutake, M. & Mori, M. (1997) J. Am. Chem. Soc. 119, 7615-7616.
41. Kondakov, D. Y. & Negishi, E. (1996) Chem. Commun., 963-964.
42. Negishi, E., Van Horn, D. E., Yoshida, T. & Rand, C. L. (1983) Organometallics 2, 563-565.
43. Gagneur, S., Montchamp, J. L. & Negishi, E. (2000) Organometallics 19, 2417-2419.
44. Dzhemilev, V. M., Vostrikova, O. S. & Sultanov, R. M. (1983) Izv. Akad. Nauk. SSSR, Ser. Khim., 218-220.
45. Boult, S. L. & Paquette, L. A. (2002) Synthesis 7, 895-900.
46. Bergot, B. J., Anderson, R. J., Schooley, D. A., Henrick, C. A. (1978) J. Chromatogr. 155, 97-105.
47. Dale, J. A., Dull, D. L. & Mosher, H. S. (1969) J. Org. Chem. 34, 2543-2549.
48. Negishi, E., Valente, L. F. & Kobayashi, M. (1980) J. Am. Chem. Soc. 102, 3298-3299.
49. Gagneur, S. & Negishi, E. (2002) in The Handbook of Organopalladium Chemistry for Organic Synthesis, ed. Negishi, E. (Wiley Interscience, New York), pp. 597-618.