A Versatile Synthesis of α-Amino Acid Derivatives via the Ugi Four-Component Condensation with a Novel Convertible Isonitrile

Synlett

Volumn , Issue 1, 2004, Pages 41-44

  Rikimaru, Kentaro ^a   Yanagisawa, Arata ^a   Kan, Toshiyuki ^a   Fukuyama, Tohru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Convertible isonitrile; N acyloxazolidinones; Thiol esters; Ugi four component condensation (4CC); amino acid derivatives

Indexed keywords

AMINO ACID DERIVATIVE; ISONITRILE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; THIOESTER;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; UGI FOUR COMPONENT CONDENSATION;

EID: 0346970836     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-43355     Document Type: Article

References (40)

1. For reviews of multicomponent reactions with isonitriles, see: (a) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51. (b) Dömling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168. (c) Gokel, G.; Lüdke, G.; Ugi, I. In Isonitrile Chemistry; Ugi, I., Ed.; Academic: New York, 1971, 145-199.
2. For reviews of multicomponent reactions with isonitriles, see: (a) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51. (b) Dömling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168. (c) Gokel, G.; Lüdke, G.; Ugi, I. In Isonitrile Chemistry; Ugi, I., Ed.; Academic: New York, 1971, 145-199.
3. For reviews of multicomponent reactions with isonitriles, see: (a) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51. (b) Dömling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168. (c) Gokel, G.; Lüdke, G.; Ugi, I. In Isonitrile Chemistry; Ugi, I., Ed.; Academic: New York, 1971, 145-199.
4. (a) Ugi, I.; Myer, R.; Fetzer, U.; Steinbrückner, C. Angew. Chem. 1959, 71, 386.
5. (b) Ugi, I.; Steinbrückner, C. Angew. Chem. 1960, 72, 267.
6. (a) Endo, A.; Yanagisawa, A.; Abe, M.; Tohma, S.; Kan, T.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 6552.
7. (b) Dömling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3200.
8. (a) For a recent example of the stereoselective Ugi 4CC reaction using a chiral amine component, see: Ross, G. F.; Herdtweck, E.; Ugi, I. Tetrahedron 2002, 58, 6127; and references therein,
9. (b) Recently, the first example of cata ytic asymmetric α-addition of isonitrile to an aldehyde was reported, see: Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2003, 125, 7825.
10. (a) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 2574.
11. (b) Strocker, A. M.; Keating, T. A.; Tempest, P. A.; Armstrong, R. W. Tetrahedron Lett. 1996, 37, 1149.
12. Lindhorst, T.; Bock, H.; Ugi, I. Tetrahedron 1999, 55, 7411.
13. Geller, J.; Ugi, I. Chem. Scr. 1983, 22, 85.
14. Mjalli, A. M. M.; Sarshar, S.; Baiga, T. J. Tetrahedron Lett. 1996, 37, 2943.
15. Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336.
16. (a) For the use of N-tert-butoxycarbonylation to activate amides, see: Flynn, D. L.; Zelle, R. E.; Grieco, P. A. J. Org. Chem. 1983, 48, 2425.
17. (b) For its application to the Ugi 4CC reaction, see: Hulme, C.; Ma, L.; Cherrier, M.-P.; Romano, J. J.; Morton, G. Tetrahedron Lett. 2000, 41, 1883.
18. For the use of N-nitrosation to activate amides, see: (a) White, E. H. J. Am. Chem. Soc. 1955, 77, 6011. (b) Evans, D. A.; Carter, P. H.; Dinsmore, C. J.; Barrow, J. C.; Katz, J. I.; Kung, D. W. Tetrahedron Lett. 1997, 38, 4535. (c) Berenguer, R.; Garcia, J.; Vilarrasa, J. Synthesis 1989, 305. (d) For its applications to the Ugi 4CC reaction, see: Isenring, H. P.; Hofheinz, W. Synthesis 1981, 385. (e) Also see: Isenring, H. P.; Hofheinz, W. Tetrahedron 1983, 39, 2591.
19. For the use of N-nitrosation to activate amides, see: (a) White, E. H. J. Am. Chem. Soc. 1955, 77, 6011. (b) Evans, D. A.; Carter, P. H.; Dinsmore, C. J.; Barrow, J. C.; Katz, J. I.; Kung, D. W. Tetrahedron Lett. 1997, 38, 4535. (c) Berenguer, R.; Garcia, J.; Vilarrasa, J. Synthesis 1989, 305. (d) For its applications to the Ugi 4CC reaction, see: Isenring, H. P.; Hofheinz, W. Synthesis 1981, 385. (e) Also see: Isenring, H. P.; Hofheinz, W. Tetrahedron 1983, 39, 2591.
20. For the use of N-nitrosation to activate amides, see: (a) White, E. H. J. Am. Chem. Soc. 1955, 77, 6011. (b) Evans, D. A.; Carter, P. H.; Dinsmore, C. J.; Barrow, J. C.; Katz, J. I.; Kung, D. W. Tetrahedron Lett. 1997, 38, 4535. (c) Berenguer, R.; Garcia, J.; Vilarrasa, J. Synthesis 1989, 305. (d) For its applications to the Ugi 4CC reaction, see: Isenring, H. P.; Hofheinz, W. Synthesis 1981, 385. (e) Also see: Isenring, H. P.; Hofheinz, W. Tetrahedron 1983, 39, 2591.
21. For the use of N-nitrosation to activate amides, see: (a) White, E. H. J. Am. Chem. Soc. 1955, 77, 6011. (b) Evans, D. A.; Carter, P. H.; Dinsmore, C. J.; Barrow, J. C.; Katz, J. I.; Kung, D. W. Tetrahedron Lett. 1997, 38, 4535. (c) Berenguer, R.; Garcia, J.; Vilarrasa, J. Synthesis 1989, 305. (d) For its applications to the Ugi 4CC reaction, see: Isenring, H. P.; Hofheinz, W. Synthesis 1981, 385. (e) Also see: Isenring, H. P.; Hofheinz, W. Tetrahedron 1983, 39, 2591.
22. For the use of N-nitrosation to activate amides, see: (a) White, E. H. J. Am. Chem. Soc. 1955, 77, 6011. (b) Evans, D. A.; Carter, P. H.; Dinsmore, C. J.; Barrow, J. C.; Katz, J. I.; Kung, D. W. Tetrahedron Lett. 1997, 38, 4535. (c) Berenguer, R.; Garcia, J.; Vilarrasa, J. Synthesis 1989, 305. (d) For its applications to the Ugi 4CC reaction, see: Isenring, H. P.; Hofheinz, W. Synthesis 1981, 385. (e) Also see: Isenring, H. P.; Hofheinz, W. Tetrahedron 1983, 39, 2591.
23. 3: 219.0895; found: 219.0900.
24. Meyers, A. I.; Collington, E. W. J. Am. Chem. Soc. 1970, 92, 6676.
25. 5: 502.2468; found: 502.2485.
26. 4: 408.2049; found: 408.2033.
27. In the absence of MS 4 Å, the reaction resulted in low yields, accompanied by the N-acylamino alcohols 12 and/or carboxylic acid 13 (Figure 2). (Equation Presented)
28. Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127.
29. For recent examples, see: Orita, A.; Nagano, Y.; Hirano, J.; Otera, J. Synlett 2001, 637; and the detailed references cited therein.
30. 3-MeOH: Sibi, M. P.; Gorikunti, U.; Liu, M. Tetrahedron 2002, 58, 8357. (d) NaOH-t-BuOH: Ito, Y.; Terashima, S. Tetrahedron 1991, 47, 2821.
31. 3-MeOH: Sibi, M. P.; Gorikunti, U.; Liu, M. Tetrahedron 2002, 58, 8357. (d) NaOH-t-BuOH: Ito, Y.; Terashima, S. Tetrahedron 1991, 47, 2821.
32. 3-MeOH: Sibi, M. P.; Gorikunti, U.; Liu, M. Tetrahedron 2002, 58, 8357. (d) NaOH-t-BuOH: Ito, Y.; Terashima, S. Tetrahedron 1991, 47, 2821.
33. 3-MeOH: Sibi, M. P.; Gorikunti, U.; Liu, M. Tetrahedron 2002, 58, 8357. (d) NaOH-t-BuOH: Ito, Y.; Terashima, S. Tetrahedron 1991, 47, 2821.
34. (a) Tokuyama, H.; Yokoshima, S.; Lin, S.-C.; Li, L.; Fukuyama, T. Synthesis 2002, 1121.
35. (b) Tokuyama, H.; Yokoshima, S.; Yamashita, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 3189.
36. (a) Nishide, K.; Ohsugi, S.; Shiraki, H.; Tamakita, H.; Node, M. Org. Lett. 2001, 3, 3121.
37. (b) Node, M.; Kumar, K.; Nishide, K.; Ohsugi, S.; Miyamoto, T. Tetrahedron Lett. 2001, 42, 9207.
38. Tokuyama, H.; Miyazaki, T.; Yokoshima, S.; Fukuyama, T. Synlett 2003, 1512.
39. 4: 495.3171; found: 495.3169.
40. In order to avoid the thiolate addition to the carbonyl group on the oxazolidinone ring, the reaction should be carried out at a temperature lower than 0 °C. Reactions at higher temperature often provided the undesired N-acylamino alcohols 12. This tendency was notably observed in compounds possessing a bulky substituent at the Z-position.