Straightforward α-carbamoylation of NADH-like dihydropyridines and enol ethers

Tetrahedron Letters

Volumn 45, Issue 42, 2004, Pages 7907-7909

  Masdeu, Carme ^a   Díaz, José Luis ^a   Miguel, Miriam ^a   Jiménez, Oscar ^a   Lavilla, Rodolfo ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Carboxamides; Dihydropyridines; Enol ethers; Isocyanides

Indexed keywords

CYANIDE; DIHYDROPYRIDINE DERIVATIVE; ETHER DERIVATIVE; HETEROCYCLIC COMPOUND; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE;

ARTICLE; CARBAMOYLATION; PROTON TRANSPORT; REACTION ANALYSIS;

EID: 4644336201     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.08.145     Document Type: Article

References (31)

1. H. Bienaymé, C. Hulme, G. Oddon, and P. Schmitt Chem. Eur. J. 6 2000 3321 3329
2. R.V.A. Orru, and M. de Greef Synthesis 2003 1471 1499
3. M.D. Burke, and S.L. Schreiber Angew. Chem., Int. Ed. 43 2004 46 58
4. I. Ugi, S. Lohberger, and R. Karl B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 2 1991 Pergamon Oxford Chapter 4
5. A. Dömling, and I. Ugi Angew. Chem., Int. Ed. 39 2000 3168 3210
6. C. Hulme, and V. Gore Curr. Med. Chem. 10 2003 51 80
7. J. Zhu Eur. J. Org. Chem. 2003 1133 1144
8. In a few examples preformed imines or enamines have been used in Ugi reactions. For instance, see: M.M. Bowers, P. Carroll, and M.M. Jouillé J. Chem. Soc., Perkin Trans. 1 1989 857 865
9. I. Ugi, and C. Steinbrückner Chem. Ber. 94 1961 2802 2814
10. For alternative carbonyl activation in Passerini-type reactions, see: D. Seebach, G. Adam, T. Gees, M. Schiess, and W. Weigand Chem. Ber. 121 1988 507 517
11. Q. Xia, and B. Ganem Org. Lett. 4 2002 1631 1634
12. S.E. Denmark, and Y. Fan J. Am. Chem. Soc. 125 2003 7825 7827
13. For the reactivity of N-acylazinium ions in Ugi-type processes, see: J.L. Díaz, M. Miguel, and R. Lavilla J. Org. Chem. 69 2004 3550 3553
14. For a recent review on the chemistry of dihydropyridines, see: R. Lavilla J. Chem. Soc., Perkin Trans. 1 2002 1141 1156
15. For the participation of dihydropyridines in MCRs, see: R. Lavilla, M.C. Bernabeu, I. Carranco, and J.L. Díaz Org. Lett. 5 2003 717 720
16. I. Carranco, J.L. Díaz, O. Jiménez, and R. Lavilla Tetrahedron Lett. 44 2003 8449 8452
17. R. Lavilla, I. Carranco, J.L. Díaz, M.C. Bernabeu, and G. de la Rosa Mol. Diversity 6 2003 171 175
18. For the use of dihydropyridines in Diversity Oriented Synthesis, see: S.J. Taylor, A.M. Taylor, and S.L. Schreiber Angew. Chem., Int. Ed. 43 2004 1681 1685
19. For the related interaction of isocyanides with pyridinium ions, which seems to proceed with considerable synthetic restrictions, see: I. Ugi, and E. Böttner Liebigs Ann. Chem. 670 1963 74 80
20. E. Marchand, and G. Morel Tetrahedron Lett. 34 1993 2319 2322
21. J.-C. Berthet, M. Nierlich, and M. Ephritikhine Eur. J. Org. Chem. 2002 375 378
22. 3O: 221.1528, found 221.1539
23. The chiral HPLC analysis (Chiralpack-AD-H; flow 1 mL/min; hexane-isopropanol-DEA 95:4.5:0.5) of the carboxamide 3a showed a 51:49 enantiomeric ratio. Retention times: 33.6 min for the first eluting isomer and 36.4 for the second eluting isomer
24. For the stereochemistry of related nucleophilic additions upon oxocarbenium ions, see: D.S. Brown, M. Bruno, R.J. Davenport, and S.V. Ley Tetrahedron 45 1989 4293 4308
25. D.M. Smith, M.B. Tran, and K.A. Woerpel J. Am. Chem. Soc. 125 2003 14149 14152
26. L. Ayala, C.G. Lucero, J.A.C. Romero, S.A. Tabacco, and K.A. Woerpel J. Am. Chem. Soc. 125 2003 15521 15528
27. For the interaction of acetals with isocyanides under acid catalysis, see: H. Pellissier, A. Meou, and G. Gil Tetrahedron Lett. 27 1986 2780 2979
28. There is a limited repertoire of procedures for the introduction of carbamoyl groups at the α-position of an enol ether. Apart from multistep transformations that involve the intermediacy of cyano groups, the photochemical addition of formamide appears to be the only direct method. For a recent reference, see: F.W. Lichtenthaler, J. Klotz, and K. Nakamura Tetrahedron: Asymmetry 14 2003 3973 3986
29. This process is, however, complex: M. Chmielewski, J.N. BeMiller, and D.P. Ceretti J. Org. Chem. 46 1981 3903 3908
30. Around 20,000 compounds belonging to these structures are listed in the Chemical Abstracts (Scifinder 2004 ed.), many of which display potent bioactivities. Particularly significant are the carbohydrate- and peptidomimetic-based scaffolds. For some leading references, see: E. Lohof, E. Planker, C. Mang, F. Burkhart, M.A. Dechantsreiter, R. Haubner, H.-J. Wester, M. Schwaiger, G. Hölzemann, S.L. Goodman, and H. Kessler Angew. Chem., Int. Ed. 39 2000 2761 2764
31. P. Thamm, H.-J. Musiol, and L. Moroder A. Felix L. Moroder C. Toniolo Houben Weyl M. Goodman Methods of Organic Chemistry Vol. E 22c 2003 Thieme Stuttgart Chapter 9.2