Asymmetric enamide hydrogenation in the synthesis of N-acetylcolchinol: a key intermediate for ZD6126

Tetrahedron Letters

Volumn 48, Issue 26, 2007, Pages 4623-4626

  Lennon, Ian C ^a   Ramsden, James A ^a   Brear, Catherine J ^b   Broady, Simon D ^b   Muir, James C ^b  

^a DOW CHEMICAL COMPANY   (United States)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

N ACETYLCOLCHINOL PHOSPHATE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; ENANTIOSELECTIVITY; HYDROGENATION; LIGAND BINDING; METAL BINDING; SYNTHESIS;

EID: 34249320471     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.04.090     Document Type: Article

References (25)

1. Micheletti G., Poli M., Borsotti P., Martinelli M., Imberti B., Taraboletti G., and Giavazzi R. Cancer Res. 63 (2003) 1534
2. Davis P.D., Dougherty G.J., Blakey D.C., Galbraith S.M., Tozer G.M., Holder A.L., Naylor M.A., Nolan J., Stratford M.R.L., Chaplin D.J., and Hill S.A. Cancer Res. 62 (2002) 7247
3. Cech J., and Šantaý F. Coll. Czech. Chem. Commun. (1949) 532
4. Sawyer J.S., and Macdonald T.L. Tetrahedron Lett. 29 (1988) 4839
5. Broady S.D., Golden M.D., Leonard J., Muir J.C., and Maudet M. Tetrahedron Lett. 48 (2007) 4627
6. Noyori R., Ohta M., Hsiao Y., Kitamura M., Ohta T., and Takaya H. J. Am. Chem. Soc. 108 (1986) 7117
7. Kitamura M., Hsiao Y., Ohta M., Tsukamoto M., Ohta T., Takaya H., and Noyori R. J. Org. Chem. 59 (1994) 297
8. Heiser B., Broger E.A., and Crameri Y. Tetrahedron: Asymmetry 2 (1991) 51
9. Tschaen D.M., Abramson L., Cai D., Desmond R., Dolling U.H., Frey L., Karaday S., Shi Y.J., and Verhoeven T.R. J. Org. Chem. 60 (1995) 4324
10. Renaud J.L., Dupau P., Hay A.-E., Guigouein M., Dixneuf P.H., and Bruneau C. Adv. Synth. Catal. 345 (2003) 230
11. Dupau P., Hay A.-E., Bruneau C., and Dixneuf P.H. Tetrahedron: Asymmetry 12 (2001) 863
12. Dupau P., Bruneau C., and Dixneuf P.H. Adv. Synth. Catal. 343 (2001) 331
13. Burk M.J., Casy G., and Johnson N.B. J. Org. Chem. 63 (1998) 6084
14. Zhang Z., Zhu G., Jiang Q., Xiao D., and Zhang X. J. Org. Chem. 64 (1999) 1774
15. Burk M.J., Wang Y.M., and Lee J.R. J. Am. Chem. Soc. 118 (1996) 5142
16. Reetz M.T., Mehler G., Meiswinkel A., and Sell T. Tetrahedron Lett. 43 (2002) 7941
17. Huang H., Zheng Z., Luo H., Bai C., Hu X., and Chen H. Org. Lett. 5 (2003) 4137
18. Van den Berg M., Haack R.M., Minmaard A.J., De Vries A.H.M., De Vries J.G., and Feringa B.L. Adv. Synth. Catal. 344 (2002) 1003
19. Jia X., Guo R., Li X., Yao X., and Chan A.S.C. Tetrahedron Lett. 43 (2002) 5541
20. Tang W., Chi Y., and Zhang X. Org. Lett. 4 (2002) 1695
21. Armstrong III J.D., Eng K.K., Keller J.L., Purick R.M., Hartner Jr. F.W., Choi W.-B., Askin D., and Volante R.P. Tetrahedron Lett. 35 (1994) 3239
22. Tang W., Wu S., and Zhang X. J. Am. Chem. Soc. 125 (2003) 9570
23. For full details of the catalytic asymmetric hydrogenation screening, see Supplementary data.
24. 3OD) δ 23.0, 31.9, 40.3, 50.9, 57.0, 61.7, 62.0, 109.4, 111.2, 114.6, 126.9, 127.1, 132.5, 137.1, 142.7, 142.8, 152.5, 154.1, 158.3, 172.8.
25. Sun Y., Landau R.N., Wang J., LeBlond C., and Blackmond D.G. J. Am. Chem. Soc. 118 (1996) 1348