Ammonium chloride promoted Ugi four-component, five-center reaction of α-substituted α-isocyano acetic acid: A strong solvent effect

Organic Letters

Volumn 6, Issue 25, 2004, Pages 4771-4774

  Bonne, Damien ^a   Dekhane, Mouloud ^b   Zhu, Jieping ^a  

^a CNRS   (France)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALDEHYDE; AMMONIUM CHLORIDE; CARBONYL DERIVATIVE; KETONE; TETRAPEPTIDE; TOLUENE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SUBSTITUTION REACTION;

EID: 11444270603     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0479388     Document Type: Article

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38. Ugi four-component, five-center reactions using α-amino acid as input: (a) Demharter, A.; Hörl, W.; Herdtweck, E.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1996, 35, 173-175. (b) Park, S. J.; Keum, G.; Kang, S. B.; Koh, H. Y.; Kim, Y.; Lee, D. H. Tetrahedron Lett. 1998, 39, 7109-7112. (c) Zimmer, R.; Ziemer, A.; Gruner, M.; Brudgam, I.; Hartl, H.; Reissig, H. U. Synthesis 2001, 1649-1658. (d) Kim, Y. B.; Choi, E. H.; Keum, G.; Kang, S. B.; Lee, D. H.; Koh, H. Y.; Kim, Y. S. Org. Lett. 2001, 3, 4149-4152. (e) Gedev, S.; Van der Eycken, J.; Fulöp, F. Org. Lett. 2002, 4, 1967-1969.
39. Ugi four-component, five-center reactions using α-amino acid as input: (a) Demharter, A.; Hörl, W.; Herdtweck, E.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1996, 35, 173-175. (b) Park, S. J.; Keum, G.; Kang, S. B.; Koh, H. Y.; Kim, Y.; Lee, D. H. Tetrahedron Lett. 1998, 39, 7109-7112. (c) Zimmer, R.; Ziemer, A.; Gruner, M.; Brudgam, I.; Hartl, H.; Reissig, H. U. Synthesis 2001, 1649-1658. (d) Kim, Y. B.; Choi, E. H.; Keum, G.; Kang, S. B.; Lee, D. H.; Koh, H. Y.; Kim, Y. S. Org. Lett. 2001, 3, 4149-4152. (e) Gedev, S.; Van der Eycken, J.; Fulöp, F. Org. Lett. 2002, 4, 1967-1969.
40. Ugi four-component, five-center reactions using α-amino acid as input: (a) Demharter, A.; Hörl, W.; Herdtweck, E.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1996, 35, 173-175. (b) Park, S. J.; Keum, G.; Kang, S. B.; Koh, H. Y.; Kim, Y.; Lee, D. H. Tetrahedron Lett. 1998, 39, 7109-7112. (c) Zimmer, R.; Ziemer, A.; Gruner, M.; Brudgam, I.; Hartl, H.; Reissig, H. U. Synthesis 2001, 1649-1658. (d) Kim, Y. B.; Choi, E. H.; Keum, G.; Kang, S. B.; Lee, D. H.; Koh, H. Y.; Kim, Y. S. Org. Lett. 2001, 3, 4149-4152. (e) Gedev, S.; Van der Eycken, J.; Fulöp, F. Org. Lett. 2002, 4, 1967-1969.
41. Ugi four-component, five-center reactions using α-amino acid as input: (a) Demharter, A.; Hörl, W.; Herdtweck, E.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1996, 35, 173-175. (b) Park, S. J.; Keum, G.; Kang, S. B.; Koh, H. Y.; Kim, Y.; Lee, D. H. Tetrahedron Lett. 1998, 39, 7109-7112. (c) Zimmer, R.; Ziemer, A.; Gruner, M.; Brudgam, I.; Hartl, H.; Reissig, H. U. Synthesis 2001, 1649-1658. (d) Kim, Y. B.; Choi, E. H.; Keum, G.; Kang, S. B.; Lee, D. H.; Koh, H. Y.; Kim, Y. S. Org. Lett. 2001, 3, 4149-4152. (e) Gedev, S.; Van der Eycken, J.; Fulöp, F. Org. Lett. 2002, 4, 1967-1969.
42. Ugi four-component, five-center reactions using α-amino acid as input: (a) Demharter, A.; Hörl, W.; Herdtweck, E.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1996, 35, 173-175. (b) Park, S. J.; Keum, G.; Kang, S. B.; Koh, H. Y.; Kim, Y.; Lee, D. H. Tetrahedron Lett. 1998, 39, 7109-7112. (c) Zimmer, R.; Ziemer, A.; Gruner, M.; Brudgam, I.; Hartl, H.; Reissig, H. U. Synthesis 2001, 1649-1658. (d) Kim, Y. B.; Choi, E. H.; Keum, G.; Kang, S. B.; Lee, D. H.; Koh, H. Y.; Kim, Y. S. Org. Lett. 2001, 3, 4149-4152. (e) Gedev, S.; Van der Eycken, J.; Fulöp, F. Org. Lett. 2002, 4, 1967-1969.
43. Ugi four-component, five-center reactions using rigid β-amino acid as input: Basso, A.; Banfi, L.; Riva, R.; Guanti, G. Tetrahedron Lett. 2004, 45, 587-590.
44. Bossio, R.; Marcaccini, S.; Paoli, P.; Pepino, R. Synthesis 1994, 672-674.
45. An additional example without specifying the yield was cited as unpublished results in the book of Ugi: Gokel, G.; Lüdke, G.; Ugi, I. In Isonitrile Chemistry, Ugi, I., Ed.; Academic Press: New York, 1971; p 159.
46. Prepared by saponification of the corresponding methyl ester. It was kept as the potassium salt since the free acid is unstable even at the refrigerator conditions. See: Takiguchi, K.; Yamada, K.; Mamoru, S.; Nanami, K.; Kimiaki, H.; Kazuo, M. Agric. Biol. Chem. 1989, 53, 77-82.
47. Ammonium chloride promoted Ugi reaction: Cristau, P.; Vors, J. P.; Zhu, J. Org. Lett. 2001, 3, 4079-4082.
48. 4, and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography (silica gel, eluent: ethyl acetate).