First general method for direct formylation of kinetically-generated ketone enolates

Organic Letters

Volumn 1, Issue 7, 1999, Pages 989-991

  Zayia, Gregory H ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007682030     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990781c     Document Type: Article

References (21)

1. (a) As precursors to α-diazo ketones, see: Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides; Wiley: New York, 1998; pp 11-14 and references therein,
2. (b) As precursors to enol thioethers, enamino ketones, enol ethers, α-formyl-α,β-unsaturated ketones, α-methylene ketones, and hydroxymethyl ketones, see: Davis, B. R.; Garratt, P. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 837-838 and references therein.
3. For reviews, see: (a) Hauser, C. R.; Swamer, F. W.; Adams, J. T. Org. React. 1954, 8, 59-196.
4. (b) House, H. O. Modern Synthetic Reactions, 2nd ed.; Benjamin: Menlo Park, 1972; Chapter 11.
5. Successful condensations include esterifications (Mander, L. N.; Sethi, S. P. Tetrahedron Lett. 1983, 24, 5425-5428), acylations (Howard, A. S.; Meerholz, C. A.; Michael, J. P. Tetrahedron Lett. 1979, 1339-1340), and trifluoroacetylations (Danheiser, R. L.; Miller, R. F.; Brisbois, R. G. Org. Synth. 1995, 73, 134-143).
6. Successful condensations include esterifications (Mander, L. N.; Sethi, S. P. Tetrahedron Lett. 1983, 24, 5425-5428), acylations (Howard, A. S.; Meerholz, C. A.; Michael, J. P. Tetrahedron Lett. 1979, 1339-1340), and trifluoroacetylations (Danheiser, R. L.; Miller, R. F.; Brisbois, R. G. Org. Synth. 1995, 73, 134-143).
7. Successful condensations include esterifications (Mander, L. N.; Sethi, S. P. Tetrahedron Lett. 1983, 24, 5425-5428), acylations (Howard, A. S.; Meerholz, C. A.; Michael, J. P. Tetrahedron Lett. 1979, 1339-1340), and trifluoroacetylations (Danheiser, R. L.; Miller, R. F.; Brisbois, R. G. Org. Synth. 1995, 73, 134-143).
8. Blackburn, G. M.; Dodds, H. L. H. J. Chem. Soc. B 1971, 826-831.
9. 2).
10. 3, enol) δ 203.9 (C=O), 178.5 (CH=COH), 97.6 (CH=COH), 42.0, 38.8, 36.6, 28.1.
11. All products are known compounds. (a) 2a: Wilson, S. R.; Misra, R. N.; Georgiadis, G. M. J. Org. Chem. 1980, 45, 2460-2468.
12. (b) 2b: Fisnerova, L.; Nemecek, O.; Musil, V. Collect. Czech. Chem. Commun. 1968, 33, 2681-2689.
13. (c) 2c: Bansal, R. C.; Browne, C. E.; Eisenbraun, E. J. J. Org. Chem. 1988, 53, 452-455.
14. (d) 2d: Johnson, W. S.; Shelberg, W. E. J. Am. Chem. Soc. 1945, 67, 1745-1754.
15. (e) 2e: Pasteur, A.; Rivière, H.; Tchoubar, B. Bull. Soc. Chim. Fr. 1965, 2328-2332.
16. (f) 2f: Labidalle, S.; Jean, E.; Moskowitz, H.; Miocque, M. Tetrahedron Lett. 1981, 22, 2869-2870. Boyer, F.; Décombe, J. Bull. Soc. Chim. Fr. 1967, 281-285.
17. (f) 2f: Labidalle, S.; Jean, E.; Moskowitz, H.; Miocque, M. Tetrahedron Lett. 1981, 22, 2869-2870. Boyer, F.; Décombe, J. Bull. Soc. Chim. Fr. 1967, 281-285.
18. (g) 2g: Tsuboi, S.; Ono, T.; Takeda, A. Heterocycles 1986, 24, 2007-2014.
19. α-Formyl ketones are sensitive materials (many extremely so). Careful handling, particularly in the workup and purification is essential.
20. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry Part B: Reactions and Synthesis, 3rd ed.; Plenum: New York, 1990; p 7.
21. Boatman, S.: Harris, T. M.: Hauser, C. R. Org. Synth. 1968, 48, 40-44.