An Improved Method for the Synthesis of a-Diazo Ketones

Journal of Organic Chemistry

Volumn 55, Issue 6, 1990, Pages 1959-1964

  Danheiser, Rick L ^a   Miller, Raymond F ^a   Brisbois, Ronald G ^a   Park1, Saung Z ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001725065     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00293a053     Document Type: Article

References (44)

1. MIT Undergraduate Research Opportunities Program participant.
2. Danheiser, R. L.; Brisbois, R. G.; Kowalczyk, J. K.; Miller, R. F. J. Am. Chem. Soc., in press.
3. For reviews of methods for the synthesis of a-diazo ketones, see: (a) Regitz, M.; Maas, G. Diazo Compounds, Properties and Synthesis; Academic Press: New York, 1986.
4. Regitz, M. In The Chemistry of Diazonium and Diazo Groups; Patai, S., Ed.; Wiley: New York, 1978; Chapter 17.
5. For discussion and examples, see (a) pp 498–499 of ref 3a.
6. Fink, J.; Regitz, M. Synthesis 1985, 569.
7. Itoh, M.; Sugihara, A. Chem. Pharm. Bull. 1969, 17, 2105.
8. Regitz, M.; Menz, F.; Liedhegener, A. Justus Liebigs Ann. Chem. 1970, 739, 174.
9. Harmon, R. E.; Sood, V. K.; Gupta, S. K. Synthesis 1974, 577.
10. Rosenquist, N. R.; Chapman, O. L. J. Org. Chem. 1976, 41, 3326 and references cited therein.
11. For reviews of diazo group transfer, see: (a) Regitz, M. Angew. Chem., Int. Ed. Engl. 1967, 6, 733.
12. Regitz, M. Synthesis 1972, 351.
13. Chapter 13 of ref 3a.
14. Diazo transfer from 2,4.6-triisopropylphenylsulfonyl azide to the enolate derivatives of hindered cyclic ketones can be achieved by using phase-transfer conditions: Lombardo, L.; Mander, L. N. Synthesis 1980, 368.
15. Evans and Britton have reported successful diazo transfer from p-nitrobenzenesulfonyl azide (PNBSA) to the enolate derivatives of an N-acyloxazolidinone and a benzyl ester: (a) Evans, D. A.; Britton, T. C. J. Am. Chem. Soc. 1987, 109, 6881.
16. Britton, T. C. Ph.D. Dissertation, Harvard University, 1987. However, we have thus far been unable to achieve efficient diazo transfer to ketone enolates employing these conditions. For example, exposure of the lithium enolate of acetophenone to 1.2 equiv of PNBSA in THF at -78 °C for 15 min gave a-diazoaceto-phenone in only 21% yield.
17. See refs 5a, 5c, and (a) Regitz, M.; Menz, F. Chem. Ber. 1968, 101, 2622.
18. Hendrickson, J. B.; Wolf, W. A. J. Org. Chem. 1968, 33, 3610.
19. Rosenberger, M.; Yates, P.; Hendrickson, J. B.; Wolf, W. Tetrahedron Lett. 1964, 2285.
20. Other indirect diazo transfer routes to a-diazo ketones have been reported involving initial activation of the ketone by benzoylation and acylation with diethyl oxalate: (a) Reference 4e.
21. Metcalf, B. W.; Jund, K.; Burkhart, J. P. Tetrahedron Lett. 1980, 21, 15.
22. Doyle, M. P.; Dorrow, R. L.; Terpstra, J. W. Rodenhouse, R. A. J. Org. Chem. 1985, 50, 1663.
23. For example, see: (a) Williams, R. M.; Im, M.-N. Tetrahedron Lett. 1988, 29, 6075.
24. Ireland, R. E.; Thompson, W. J. J. Org. Chem. 1979, 44, 3041.
25. Schow, S. R.; Bloom, J. D.; Thompson, A. S.; Win-zenberg, K. N.; Smith, A. B. J. Am. Chem. Soc. 1986, 108, 2662.
26. Taber, D. F.; Ruckle, R. E., Jr.; Hennessy, M. J. Org. Chem. 1986, 51, 4077.
27. Lowe, G.; Ramsay, M. V. J. Chem. Soc., Perkin Trans. 1 1973, 479.
28. Stork, G.; Szajewski, R. P. J. Am. Chem. Soc. 1974, 96, 5787.
29. Boyer, J. H.; Mack, C. H.; Goebel, N.; Morgan, L. R., Jr. J. Org. Chem. 1958, 23, 1051.
30. For example (a) p-carboxybenzenesulfonyl azide: ref 8b.
31. Polymer-bound tosyl azide: Roush, W. R.; Feitler, D.; Rebek, J. Tetrahedron Lett. 1974, 1391.
32. p-Dodecylbenzenesulfonyl azide: Hazen, G. G.; Weinstock, L. M.; Connell, R.; Bollinger, F. W. Synth. Commun. 1981, 11, 947.
33. p-Acetamidobenzenesulfonyl azide: Baum, J. S.; Shook, D. A.; Davies, H. M. L.; Smith, H. D. Synth. Commun. 1987, 17, 1709.
34. Olofson, R. A.; Dougherty, C. M. J. Am. Chem. Soc. 1973, 95, 582.
35. Stork, G.; Hudrlik, P. F. J. Am. Chem. Soc. 1968, 90, 4464.
36. Bachmann, W. E.; Struve, W. S. Org. React. 1942, 1, 38.
37. Meier, H.; Zeller, K.-P. Angew. Chem., Int. Ed. Engl. 1975, 14, 32.
38. Maas, G. Top. Curr. Chem. 1987, 137, 75.
39. Steinberg, G. M.; Lieske, C. N.; Ash, A. B.; Blumbergs, P. U.S. Patent 3729S558, 1973.
40. Horner, L.; Kirmse, W.; Muth, K. Chem. Ber. 1958, 91, 430.
41. Tamura, Y.; Ikeda, H.; Mukai, C.; Bayomi, S. M.; Ikeda, M. Chem. Pharm. Bull. 1980, 28, 3430.
42. Scott, L. T.; Minton, M. A.; Kirms, M. A. J. Am. Chem. Soc. 1980, 102, 6311.
43. Ogawa, K.; Terada, T.; Mur an aka, Y.; Hamakawa, T.; Hashimoto, S.; Fujii, S. Chem. Pharm. Bull. 1986, 34, 3252.
44. Taniguchi, Y.; Inanaga, J.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1981, 54, 3229.