Enhanced diastereoselectivity in the asymmetric Ugi reaction using a new 'convertible' isonitrile

Journal of Organic Chemistry

Volumn 64, Issue 2, 1999, Pages 336-337

  Linderman, Russell J ^a   Binet, Sophie ^a   Petrich, Samantha R ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; ISONITRILE DERIVATIVE;

ARTICLE; DIASTEREOISOMER; HYDROLYSIS; REACTION ANALYSIS;

EID: 0033593261     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982186e     Document Type: Article

References (22)

1. (a) Ugi, I. Angew. Chem., Intl. Ed. Engl. 1982, 21, 810-819.
2. (b) Ugi, I. J. Prakt. Chem. 1997, 339, 499-516.
3. (a) Mjalli, A. M. M.; Sarshar, S.; Baiga, T. J. Tetrahedron Lett. 1996, 37, 2943-2946.
4. (b) Hanusch-Kompa, C.; Ugi, I. Tetrahedron Lett. 1998, 39, 2725-2728.
5. (c) Short, K. M.; Mjalli, A. M. M. Tetrahedron Lett. 1997, 38, 359-362.
6. (d) Short, K. M.; Ching, B. W.; Mjalli, A. M. M. Tetrahedron Lett. 1996, 37, 7489-7492.
7. (e) Bienayme, H.; Bouzid, K. Tetrahedron Lett. 1998, 39, 2735-2738.
8. (f) Hulme, C.; Morrissette, M. W.; Volz, F. A.; Burns, C. J. Tetrahedron Lett. 1998, 39, 1113-1116.
9. (a) Bock, H.; Ugi, I. J. Prakt. Chem. 1997, 339, 385-389.
10. (b) Ziegler, T.; Schlomer, R.; Koch, C. Tetrahedron Lett. 1998, 39, 5957-5960.
11. Sigmuller, F.; Herrmann, R.; Ugi, I. Tetrahedron 1986, 42, 5931-5940.
12. (a) Galactosylamine for (R)-amino acid synthesis: Kunz, H.; Pfrengle, W. Tetrahedron 1988, 44, 5487-5494.
13. (b) Arabinosylamine for (S)-amino acid synthesis: Kunz, H.; Pfrengle, W.; Sager, W. Tetrahedron Lett. 1989, 30, 4109-4110.
14. Lehnhoff, S.; Goebel, M.;Karl, R. M.; Klosel, R.;Ugi, I. Angew. Chem., Intl. Ed. Engl. 1995, 34, 1104-1107.
15. For selective hydrolysis of secondary amide Ugi products via initial chemical conversion to an oxazolidinone, see ref 2a and Geller, J.; Ugi, I. Chem. Scr. 1983, 22, 85-89.
16. (a) Strocker, A. M.; Keating, T. A.; Tempest, P. A.; Armstrong, R. W. Tetrahedron Lett. 1998, 37, 1149-1152.
17. (b) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 2574-2583.
18. (c) Keating, T. A.; Armstrong, R. W. J. Org. Chem. 1996, 61, 8935-8939.
19. Evans, D. A.; Takasc, J. M. Tetrahedron Lett. 1980, 21, 4233-36. For a recent example, see: Pippel, D. J.; Curtis, M. D.; Du, H.; Beak, P. J. Org. Chem. 1998, 63, 2-3.
20. Evans, D. A.; Takasc, J. M. Tetrahedron Lett. 1980, 21, 4233-36. For a recent example, see: Pippel, D. J.; Curtis, M. D.; Du, H.; Beak, P. J. Org. Chem. 1998, 63, 2-3.
21. Vinyl fluorides are potential peptide isosteres. See, (a) Allmendinger, T.; Furet, P.; Hungerbuhler, E. Tetrahedron Lett. 1990, 31, 7297-7300. (b) Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107-3111.
22. Vinyl fluorides are potential peptide isosteres. See, (a) Allmendinger, T.; Furet, P.; Hungerbuhler, E. Tetrahedron Lett. 1990, 31, 7297-7300. (b) Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107-3111.