Electroreductive coupling of aliphatic amides. A useful method for the synthesis of α-amino ketones

Tetrahedron Letters

Volumn 39, Issue 34, 1998, Pages 6199-6202

  Kashimura, Shigenori ^a   Ishifune, Manabu ^a   Murai, Yoshihiro ^a   Murase, Hiroaki ^a,b   Shimomura, Masatoshi ^a   Shono, Tatsuya ^a  

^a KINKI UNIVERSITY   (Japan)

^b OSAKA GAS CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; KETONE DERIVATIVE;

ARTICLE; ELECTROCHEMISTRY; ELECTRODE; HYDROLYSIS; REACTION ANALYSIS; SYNTHESIS;

EID: 0032552091     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01274-X     Document Type: Article

References (13)

1. 6) Shono, T.; Masuda, H.; Murase, H.; Shimomura, M.; Kashimura, S. J. Org. Chem. 1992, 57, 1061.
2. 7) Kashimura, S.; Murai, Y.; Ishifune, M.; Masuda, H.; M.; Murase, H.; Shono, T. Tetrahedron Lett. 1995, 36, 4805.
3. 8) Kashimura, S.; Muraai, Y.; Ishifune, M.; Washika, C.; Yoshiwara, D.; Kataoka, Y.; Murase, H.; Shono, T. Tetrahedron Lett. 1997, 38, 6717.
4. 9) It has been reported that the reduction of an aliphatic amide with Na metal was unsuccessful 10 and that of an aromatic amide under similar reduction conditions did not give the coupling product. 11
5. 10) Lynn, J.W.; English, J. J. Am. Chem. Soc. 1951, 73, 4284.
6. 11) Bourgeois, P.; Duffaut, N. J. Organometal. Chem. 1972, 35, 63.
7. 2Mg and this salt was insoluble in THF and hence, 2e was not reduced under the conditions of electroreduction.
8. 29NO: C,76.44;H, 11.63; N, 5.57. Found: C,76.34;H, 11.92; N, 5.48.
9. 14) Bloomfield, J.J.; Owsley, D.C. J. Org. Chem. 1975, 40, 393.
10. 23NSi: 173.1600; Found: 173.1612.
11. 11
12. 18
13. 18) Kuwajima, I,; Sato, T.; Minami, N.; Abe, T. Tetrahedron Lett. 1976, 1591.