Bis(2-t-butylphenyl)phosphonoacetamides for the highly cis-selective synthesis of α,β-unsaturated amides

Tetrahedron Letters

Volumn 50, Issue 40, 2009, Pages 5689-5691

  Ando, Kaori ^a   Nagaya, Shigeo ^a   Tarumi, Yuko ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; BIS(2 TERT BUTYLPHENYL)PHOSPHONOACETAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARBUZOV REACTION; ARTICLE; CIS ISOMER; HORNER WADSWORTH EMMONS REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 68749089734     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.07.130     Document Type: Article

References (27)

1. Albert B.J., Sivaramakrishnan A., Naka T., Czaicki N.L., and Koide K. J. Am. Chem. Soc. 129 (2007) 2648-2659
2. Petri A.F., Sasse F., and Maier M.E. Eur. J. Org. Chem. (2005) 1865-1875
3. Chakraborty T.K., and Laxman P. Tetrahedron Lett. 44 (2003) 4989-4992
4. Ashimori A., Bachand B., Calter M.A., Govek S.P., Overman L.E., and Poon D.J. J. Am. Chem. Soc. 120 (1998) 6488-6499
5. Davis F.A., Qi H., and Sundarababu G. Tetrahedron 56 (2000) 5303-5310
6. Carey J.S. J. Org. Chem. 66 (2001) 2526-2529
7. Ando K. Synlett (2001) 1272-1274
8. Fortin S., Dupont F., and Deslongchamps P. J. Org. Chem. 67 (2002) 5437-5439
9. Kojima S., Hidaka T., Ohba Y., and Ohkata K. Phosphorus, Sulfur and Silicon 177 (2002) 729-732
10. Kojima S., Hidaka T., and Yamakawa A. Chem. Lett. 34 (2005) 470-471
11. Peterson reaction:. Kojima S., Inai H., Hidaka T., and Ohkata K. Chem. Commun. (2000) 1795-1796
12. Ando K. Tetrahedron Lett. 36 (1995) 4105-4108
13. Ando K. J. Org. Chem. 62 (1997) 1934-1939
14. Ando K. J. Org. Chem. 63 (1998) 8411-8416
15. Ando K. J. Org. Chem. 64 (1999) 8406-8408
16. Ando K., Oishi T., Hirama M., Ohno H., and Ibuka T. J. Org. Chem. 65 (2000) 4745-4749
17. Touchard F.P., Capelle N., and Mercier M. Adv. Synth. Catal. 347 (2005) 707-711
18. Nahm S., and Weinreb S.M. Tetrahedron Lett. 22 (1981) 3815-3818
19. Evans D.A., Kaldor S.W., Jones T.K., Clardy J., and Stout T.J. J. Am. Chem. Soc. 112 (1990) 7001-7031
20. Nuzillard J., Boumendjel A., and Massiot G. Tetrahedron Lett. 30 (1989) 3779-3780
21. Netz D.F., and Seidel J.L. Tetrahedron Lett. 33 (1992) 1957-1958
22. Martin R., Romea P., Tey C., Urpi F., and Vilarrasa J. Synlett (1997) 1414-1415
23. Kurosu M., and Kishi Y. Tetrahedron Lett. 39 (1998) 4793-4796
24. 1H NMR spectra and mass spectroscopy. The cis:trans ratios were determined by integration of the vinyl proton signals.
25. Mechelke M.F., and Meyers A.I. Tetrahedron Lett. 41 (2000) 4339-4342
26. 2POEt (6.890 g, 18.4 mmol) and 8 (3.351 g, 18.4 mmol) was heated at 150 °C under Ar atmosphere for 8 h. Column chromatography (silica gel/33% AcOEt in hexane) gave 7 (4.573 g, 56%) as a colorless powder (mp 62.7-63.5 °C). The reagents 4b-d were prepared in the same way.
27. 4), and concentrated. The residue was purified by flash chromatography (50% AcOEt in hexane) to give amide 9 (0.0729 g, 96%) as a colorless oil.