Facile synthesis of aryl α-keto esters via the reaction of aryl diazoacetate with H2O and DEAD

Synlett

Volumn , Issue 15, 2006, Pages 2486-2488

  Guo, Zhenqiu ^a,b   Huang, Haoxi ^a,b   Fu, Qingquan ^a,b   Hu, Wenhao ^a  

^a CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

diazoacetate; keto ester; Fragmentation; Oxonium ylide

Indexed keywords

ACETIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; WATER;

ARTICLE; CATALYSIS; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 33749334805     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950412     Document Type: Article

References (31)

1. For applications of aryl α-keto esters, see: (a) Boeykens, M.; De Kimpe, N.; Tehrani, K. A. J. Org. Chem. 1994, 59, 6973.
2. (b) Jacobson, I. C.; Prabhakar Reddy, G. Tetrahedron Lett. 1996, 37, 8263.
3. (c) Akiyama, T.; Suzuki, M. Chem. Commun. 1997, 2357.
4. (d) Petronijevic, F.; Hart, A. C.; Paquette, L. A. Tetrahedron Lett. 2006, 47, 1741.
5. (e) Veeraraghavan Ramachandran, P.; Pitre, S.; Brown, H. C. J. Org. Chem. 2002, 67, 5315.
6. (f) Jiang, B.; Chen, Z.-L.; Tang, X.-X. Org. Lett. 2002, 4, 3451.
7. (g) Wang, G.-Y.; Hu, J.-B.; Zhao, G. Tetrahedron: Asymmetry 2004, 15, 807.
8. (h) Periasamy, M.; Sivakumar, S.; Narsi Reddy, M. Synthesis 2003, 1965.
9. (i) Christensen, C.; Juhl, K.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 4875.
10. Axten, J. M.; Krim, L.; Kung, H. F.; Winkler, J. D. J. Org. Chem. 1998, 63, 9628.
11. (a) Babudri, F.; Fiandanese, V.; Marchese, G.; Punzi, A. Tetrahedron 1996, 52, 13513; and references cited therein.
12. (b) Nimitz, J.; Mosher, H. S. J. Org. Chem. 1981, 46, 211.
13. (c) de las Heras, M. A.; Vaquero, J. J.; Garcia-Navio, J. L.; Alvarez-Builla, J. J. Org. Chem. 1996, 61, 9009.
14. (a) Matsunaka, K.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1999, 40, 2165.
15. (b) Wentzel, B. B.; Donners, M. P. J.; Alsters, P. L.; Feitersa, M. C.; Nolte, R. J. M. Tetrahedron 2000, 56, 7797.
16. (c) Velusamy, S.; Punniyamurthy, T. Tetrahedron Lett. 2003, 44, 8955.
17. Micetich, R. G. Org. Prep. Proced. Int. 1970, 2, 249.
18. (a) Tatlock, J. H. J. Org. Chem. 1995, 60, 6221.
19. (b) Li, L.-S.; Wu, Y.-L. Tetrahedron Lett. 2002, 43, 2427.
20. Thasana, N.; Prachyawarakorn, V.; Tontoolarug, S.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1019.
21. (a) Wasserman, H. H.; Hot, W. B. J. Org. Chem. 1994, 59, 4364.
22. (b) Wong, M.-K.; Yu, C.-W.; Yuen, W.-H.; Yang, D. J. Org. Chem. 2001, 66, 3606.
23. Ma, M.; Li, C.-K.; Peng, L.-L.; Xie, F.; Zhang, X.; Wang, J.-B. Tetrahedron Lett. 2005, 46, 3927.
24. (a) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley: New York, 1998.
25. (b) Nitrogen, Oxygen and Sulfur Ylide Chemistry; Clark, J. S., Ed.; Oxford University Press: Oxford, 2002.
26. Lu, C.-D.; Liu, H.; Chen, Z.-Y.; Hu, W.-H.; Mi, A.-Q. Org. Lett. 2005, 7, 83.
27. Huang, H.-X.; Wang, Y.-H.; Chen, Z.-Y.; Hu, W.-H. Synlett 2005, 2498.
28. (a) BuiNguyen, M. H.; Dahn, H.; Mcgarrity, J. F. Helv. Chim. Acta 1980, 63, 63.
29. (b) Jones, J.; Kresge, A. J. J. Org. Chem. 1993, 58, 2658.
30. 2O (59.4 mL, 3.3 mmol) and DEAD (574.7 mg, 3.3 mmol) was addedphenyl diazoacetate 1a (528.5 mg, 3 mmol) in 18 mL of toluene over 1 h via a syringe pump. After stirring for additional 3 h, the reaction mixture was cooled to r.t. and the solvent was removed. The crude product was purified by flash chromatography on silica gel by using 3% EtOAc-light PE as eluent to give an white oil 2a (448.2 mg, 2.73 mmol), yield 91%.
31. +.