DBU-catalyzed condensation of acyldiazomethanes to aldehydes in water and a new approach to ethyl β-hydroxy α-arylacrylates

Tetrahedron Letters

Volumn 48, Issue 7, 2007, Pages 1147-1149

  Xiao, Fengping ^a   Liu, Yu ^a   Wang, Jianbo ^a  

^a BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

Author keywords

1,2 Aryl shift; DBU catalyzed condensation; Diazo compounds; Rh(II) carbene

Indexed keywords

ACRYLIC ACID DERIVATIVE; ACYLDIAZOMETHANE DERIVATIVE; ALDEHYDE DERIVATIVE; DIAZOMETHANE; RHODIUM DERIVATIVE; SILOXANE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 33846291829     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.062     Document Type: Article

References (34)

1. Doyle M.P., McKervey M.A., and Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds (1998), Wiley-Interscience, New York
2. Schollkopf U., Frasnelli H., and Hoppe D. Angew. Chem., Int. Ed. Engl. 9 (1970) 300
3. Wenkert E., and McPherson A.A. J. Am. Chem. Soc. 94 (1972) 8084
4. Burkoth T.L. Tetrahedron Lett. 57 (1969) 5049
5. Woolsey N.F., and Khalil M.H. J. Org. Chem. 37 (1972) 2405
6. Schollkopf U., Banhidai B., Frasnelli H., Meyer R., and Beckhaus H.L. Ann. Chem. (1974) 1767
7. Pellicciari R., and Natalini B. J. Chem. Soc., Perkin Trans. 1 (1977) 1882
8. Moody C.J., and Taylor R.J. Tetrahedron Lett. 28 (1987) 5351
9. Pellicciari R., Natalini B., Sadeghpour B.M., Marinozzi M., Snyder J.P., Williamson B.L., Kuethe J.T., and Padwa A. J. Am. Chem. Soc. 118 (1996) 1
10. Ikota N., Takamura N., Young S.D., and Ganem B. Tetrahedron Lett. 22 (1981) 4163
11. Holmquist C.R., and Roskamp E.J. J. Org. Chem. 54 (1989) 3258
12. Mahmood S.J., and Hossain M.M. J. Org. Chem. 63 (1998) 3333
13. Kanemasa S., Kannai T., Araki T., and Wada E. Tetrahedron Lett. 40 (1999) 5055
14. Dudley M.E., Morshed Md.M., Brennan C.L., Islam M.S., Ahmad M.S., Atuu M.-R., Branstetter B., and Hossain M.M. J. Org. Chem. 69 (2004) 7599
15. For an account, see:. Zhao Y., and Wang J. Synlett (2005) 2886
16. Jiang N., Qu Z., and Wang J. Org. Lett. 3 (2001) 2989
17. Shi W., Jiang N., Zhang S., Wu W., Du D., and Wang J. Org. Lett. 5 (2003) 2243
18. Shi W., Zhang B., Liu B., Xu F., Xiao F., Zhang J., Zhang S., and Wang J. Tetrahedron Lett. 45 (2004) 4563
19. Xiao F., Zhang Z., Zhang J., and Wang J. Tetrahedron Lett. 46 (2005) 8873
20. Shi W., Xiao F., and Wang J. J. Org. Chem. 70 (2005) 4318
21. Shi W., Zhang B., Zhang J., Liu B., Zhang S., and Wang J. Org. Lett. 7 (2005) 3103
22. Xu F., Shi W., and Wang J. J. Org. Chem. 70 (2005) 4218
23. Xu F., Zhang S., Wu X., Liu Y., Shi W., and Wang J. Org. Lett. 8 (2006) 3207
24. Xiao F., and Wang J. J. Org. Chem. 71 (2006) 5789
25. Vitale M., Lecourt T., Sheldon C.G., and Aggarwal V.K. J. Am. Chem. Soc. 128 (2006) 2524
26. Arai S., Hasegawa K., and Nishida A. Tetrahedron Lett. 45 (2004) 1023
27. Jiang N., and Wang J. Tetrahedron Lett. 43 (2002) 1285
28. General procedure for DBU-promoted reactions of 1a-q in water. To a stirring solution of water (1 mL) containing EDA (1.2 mmol) and aldehyde (1 mmol), DBU (30 mol %) was added. The reaction mixture was stirred at room temperature until completion of the reaction. Usual workup afforded the pure 2a-q.
29. For recent report on 1,3-dicarbonyl compounds, see:. Atuu M.R., Mahmood S.J., Laib F., and Hossain M.M. Tetrahedron: Asymmetry 15 (2004) 3091
30. Mahmood S.J., Brennan C., and Hossain M.M. Synthesis 13 (2002) 1807
31. Schmittel M., and Ammon H. Eur. J. Org. Chem. 5 (1998) 785
32. Kamaya H., Sato M., and Kaneko C. Tetrahedron Lett. 38 (1997) 587
33. 3SiCl (1.1 mmol) was added via syringe at 0 °C. The mixture was allowed to stir for 2 h between 0 °C and room temperature. Usual workup afforded the pure β-siloxy diazo compounds.
34. 4 (0.5 mol %) was added diazo compound 4a-l (1.0 mmol). The reaction mixture was stirred at room temperature. When the diazo compound disappeared as indicated by TLC, the solvent was removed under reduced pressure to give a crude residue, which was purified by silica gel column chromatography.