Catalytic C-amidoalkylations: Synthesis of β-amido aldehydes by three-component condensations

Chemical Communications

Volumn , Issue 1, 1998, Pages 83-84

  Marson, Charles M ^a,b   Fallah, Asad ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0141542769     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a707484k     Document Type: Article

References (21)

1. H. E. Zaugg, Synthesis, 1984, 85;
2. H. E. Zaugg, Synthesis, 1984, 181.
3. H. E. Zaugg and W. B. Martin, Org. React., 1965, 14, 52.
4. T. Shono, Y. Matsumura and K. Tsubata, J. Am. Chem. Soc., 1981, 103, 1172.
5. C. M. Marson, U. Grabowska, T. Walsgrove, D. S. Eggleston and P. W. Baures, J. Org. Chem., 1991, 56, 2603;
6. C. M. Marson, U. Grabowska, T. Walsgrove, D. S. Eggleston and P. W. Baures, J. Org. Chem., 1994, 59, 284.
7. C. M. Marson, U. Grabowska and T. Walsgrove, J. Org. Chem., 1992, 57, 5045;
8. C. M. Marson, U. Grabowska, A. Fallah, T. Walsgrove, D. S. Eggleston and P. W. Baures, J. Org. Chem., 1994, 59, 291.
9. P. J. Stang and M. R. White, Aldrichim. Acta, 1983, 16, 15.
10. C. M. Marson and A. Fallah, Tetrahedron Lett., 1994, 35, 293.
11. (a) P. A. Tempest, S. D. Brown and R. W. Armstrong, Angew. Chem., Int. Ed. Engl., 1996, 35, 640;
12. (b) G. H. Posner, Chem. Rev., 1986, 86, 831.
13. S. G. Davies and T. D. McCarthy, Synlett, 1995, 700;
14. I. E. Markó and A. Chesney, Synlett, 1992, 275.
15. B. F. Bonini, M. Comes-Franchini, G. Mazzanti, A. Ricci and M. Sala, J. Org. Chem., 1996, 61, 7242.
16. T. Suami, K. Tadano and S. Horiuchi, Bull. Chem. Soc. Jpn., 1975, 48, 2895.
17. 1H NMR spectra of the separated diastereoisomeric acids obtained by aerial oxidation of the aldehydes in entry 1 exhibit couplings for the vicinal methine hydrogen atoms of 10 and 5 Hz (isolated as the minor diastereoisomer), and 3 and 5 Hz (major diastereoisomer). The former values are consistent with the syn-isomer in a preferred conformation in which the amido and aldehyde groups are antiperiplanar, and the methine hydrogen atoms are disposed trans (J = 10 Hz). ('syn' refers to relation of α-alkyl and β-amido groups, the aldehyde being drawn as part of the 'backbone' of the product.) Such assignments are consistent with those for other β-amido carbonyl compounds: H. Estermann and D. Seebach, Helv. Chim. Acta, 1988, 71, 1824.
18. H. Zimmerman and M. Traxler, J. Am. Chem. Soc., 1957, 79, 1920.
19. J. F. Walker, Formaldehyde, Reinhold, New York, NY, 3rd edn., 1964, pp. 359-414.
20. E. E. Gilbert, Synthesis, 1972, 30;
21. W. A. Noyes and D. B. Forman, J. Am. Chem. Soc., 1933, 55, 3493.