First Carbamates Conversion to Amides by Simple Alkyl Group Transfer from Trialkylalanes

Organic Letters

Volumn 6, Issue 3, 2004, Pages 381-383

  El Kaim, Laurent ^a   Grimaud, Laurence ^a   Lee, Anabelle ^a   Perroux, Yannick ^a   Tirla, Cornelia ^a  

^a Ecole Nationale Superieure de Techniques Avancees   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKANE DERIVATIVE; ALKYL GROUP; ALUMINUM DERIVATIVE; AMIDE; CARBAMIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTECTION;

EID: 1342285485     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036234f     Document Type: Article

References (15)

1. For typical examples see: (a) Nahm, S.; Weinreb, S. Tetrahedron Lett. 1981, 22, 3815-3818. (b) Hlasta, D.; Court, J. Tetrahedron Lett. 1989, 30, 1773-1776. (c) Chung, E.; Cho, C. W.; Ahn, K. J. Org. Chem. 1998, 63, 7590-7591.
2. For typical examples see: (a) Nahm, S.; Weinreb, S. Tetrahedron Lett. 1981, 22, 3815-3818. (b) Hlasta, D.; Court, J. Tetrahedron Lett. 1989, 30, 1773-1776. (c) Chung, E.; Cho, C. W.; Ahn, K. J. Org. Chem. 1998, 63, 7590-7591.
3. For typical examples see: (a) Nahm, S.; Weinreb, S. Tetrahedron Lett. 1981, 22, 3815-3818. (b) Hlasta, D.; Court, J. Tetrahedron Lett. 1989, 30, 1773-1776. (c) Chung, E.; Cho, C. W.; Ahn, K. J. Org. Chem. 1998, 63, 7590-7591.
4. (a) Hubbard, J. S.; Harris, T. M. J. Org. Chem. 1981, 46, 2566-2570.
5. (b) Shono, T.; Kise, N.; Sanda, F.; Ohi, S.; Tsubata, K. Tetrahedron Lett. 1988, 29, 231-234.
6. (c) White, J. D.; Blakemore, P. R.; Milicevic, S.; Choudhry, S. C.; Cupano, J.; Serico, L. Org. Lett. 2002, 4, 1803-1806.
7. (d) Tay, M. K.; About-Jaudet, E.; Savignac, P. Tetrahedron 1989, 45, 4415-4430.
8. El Kaim, L.; Grimaud, L.; Perroux, Y.; Tirla, C. J. Org. Chem. 2003, 68, 8733-8735.
9. (a) Li, W. R.; Yo, Y. C.; Lin, Y. S. Tetrahedron 2000, 56, 8867-8875.
10. (b) Nazih, A.; Heissler, D. Synthesis 2002, 203-206.
11. (c) Ihara, M.; Hirabayashi, A.; Taniguchi, N.; Fukumoto, K. Heterocycles 1992, 33, 851-858.
12. For typical examples of carbamates conversion to acetamides, see: (a) Masatshi, K.; Kunitomo, A.; Toshiyuki, K.; Masanori, H.; Tokushi, H.; Yoshiyuki, A.; Tadashi, M.; Masafuni, A.; Noriyoshi, N.; Makio, O.; Yukio, H. J. Med. Chem. 2000, 43, 2946-2961. (b) Tanida, H.; Tsuji, T.; Irie, T. J. Org. Chem. 1966, 31, 3941-3947.
13. For typical examples of carbamates conversion to acetamides, see: (a) Masatshi, K.; Kunitomo, A.; Toshiyuki, K.; Masanori, H.; Tokushi, H.; Yoshiyuki, A.; Tadashi, M.; Masafuni, A.; Noriyoshi, N.; Makio, O.; Yukio, H. J. Med. Chem. 2000, 43, 2946-2961. (b) Tanida, H.; Tsuji, T.; Irie, T. J. Org. Chem. 1966, 31, 3941-3947.
14. Though adducts between alanes and carbamates have been described as solids and shown to exhibit a reversible Al shift from N to O (carbonyl), the lack of reactivity of 1g makes us believe that adducts type A could be the reactive intermediate in this reaction: Hirabayashi, T.; Sakakibara, T.; Ishii, Y. J. Organomet. Chem. 1971, 32, C5-C6.
15. These additions are described using an ether solution of HCl as catalyst. A few drops of concentrated HCl in water gives also satisfying results: Benalil, A.; Roby, P.; Carboni, B.; Vaultier, M. Synthesis 1991, 787-788.