Passerini and ugi reactions of anomeric glucosyl isonitriles

Tetrahedron Letters

Volumn 39, Issue 33, 1998, Pages 5957-5960

  Ziegler, Thomas ^a   Schlömer, Rolf ^a   Koch, Christoph ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ALDEHYDE DERIVATIVE; AMINE; BUTYRALDEHYDE; CARBOXYLIC ACID DERIVATIVE; ISONITRILE DERIVATIVE;

ARTICLE; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032514429     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01216-7     Document Type: Article

References (23)

1. 1. (a) Boullanger, P.; Descotes, G., Tetrahedron Lett., 1976, 38, 3427-3430.
2. (b) Boullanger, P.; Marmet, D.; Descotes, G., Tetrahedron, 1979, 35, 163-167.
3. 2. Nolte, R.J.M.; van Zomeren, J.A.J.; Zwikker, J.W., J. Org. Chem., 1978, 43, 1972-1975.
4. 3. (a) For a review of the literature up to 1983 see: Witzak, Z.J., J. Carbohydr. Chem., 1984, 3, 359-380.
5. (b) Witczak, Z.J., Tetrahedron Lett., 1986, 27, 155-158.
6. (c) Ewing, D.F.; Hiebl, J.; Humble, R.W.; Mackenzie, G.; Raynor, A.; Zbiral, E., J. Carbohydr. Chem., 1993, 12, 923-932.
7. 4. For reviews on Ugi reactions see: (a) Gökel, G.; Lüdke, G.; Ugi, I. (Eds.) in Isonitrile Chemistry, Academic Press, New York 1971, pp. 145-199;
8. (b) Ugi, I.; Dömling, A.; Hörl, W., Endeavour, 1994,18, 115-122.
9. 5. For the use of glycosyl amines in Ugi reactions see: (a) Kunz, H., Houben-Weyl, 1996, E 21, 1945-1952.
10. (b) Lehnhoff, S.; Goebel, M.; Karl, R.M.; Klösel, R.; Ugi, I., Angew. Chem., 1995, 107, 1208-1211; Angew. Chem. Int. Ed. Engl., 1995, 34, 1104-1107.
11. (b) Lehnhoff, S.; Goebel, M.; Karl, R.M.; Klösel, R.; Ugi, I., Angew. Chem., 1995, 107, 1208-1211; Angew. Chem. Int. Ed. Engl., 1995, 34, 1104-1107.
12. 6. (a) Keating, T.A.; Armstrong, R.W., J. Am. Chem. Soc., 1995, 117, 7842-7843;
13. (b) Tempest, P.A.; Brown, S.D.; Armstrong, R.W., Angew. Chem., 1996, 108, 689-691; Angew. Chem. Int. Ed. Engl., 1996, 35, 640-642;
14. (b) Tempest, P.A.; Brown, S.D.; Armstrong, R.W., Angew. Chem., 1996, 108, 689-691; Angew. Chem. Int. Ed. Engl., 1996, 35, 640-642;
15. (c) Ugi, I; Dömling, A.; Gruber, B.; Almstetter, M., Croatia Chem. Acta, 1997, 70, 631-647.
16. 7. Tropper, F.D.; Andersson, F.O.; Braun, S.; Roy, R., Synthesis 1992, 618-620.
17. 8. Glaudemans, C.PJ; Fletcher, H.G., Methods Carbohydr. Chem., 1972, 6, 373-376.
18. 9. Aebischer, B.M.; Hanssen, H.W.; Vasella, A.; Schweizer, W.B., J. Chem. Soc. Perkin Trans. 1, 1982, 2139-2147.
19. 10. Ugi, I.; Skorna, G., Angew. Chem., 1977, 89, 267-268; Angew. Chem. Int. Ed. Engl., 1977, 16, 259.
20. 10. Ugi, I.; Skorna, G., Angew. Chem., 1977, 89, 267-268; Angew. Chem. Int. Ed. Engl., 1977, 16, 259.
21. 11. Ugi, I. in The Peptides (Gross, E.; Meienhofer, J., Eds.), Academic press, New York 1980, pp.365.
22. 12. All compounds gave satisfactory elemental analyses. D.r. values were determined by NMR spectroscopy and HPLC analysis of the diastereomeric products.
23. 2Ph), 3.89-3.97 (m, 2 H, H-14), 3.67-3.76 (m, 4 H, H-3,5.6), 3.51-3.55 (m, 1 H, H-4), 3.36-3.43 (m, 1 H, H-2), 3.02-3.11 (m, 2 H, H-11), 2.41-2.56 (brs, 1 H, H-9), 1.72-1.94 (brs, 1 H, H-8), 1.37-1.61 (m, 2 H, H-12), 1.45 (s, 9 H, Boc), 0.77-0.98 (2 d, 6 H, H-10), 0.73 (t, 3 H, J = 7.3 Hz, H-13).