4-Isocyanopermethylbutane-1,1,3-triol (IPB): A convertible isonitrile for multicomponent reactions

Tetrahedron Letters

Volumn 53, Issue 40, 2012, Pages 5360-5363

  Neves Filho, Ricardo A W ^a   Stark, Sebastian ^a   Morejon, Micjel C ^a   Westermann, Bernhard ^a,b   Wessjohann, Ludger A ^a,b  

^a LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

^b MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

Activated amides; Activated carboxylic acids; Formate carbanion equivalent; Functional group interconversions; Isocyanides; N Acylpyrroles; Passerini reaction; Ugi reaction; Ugi Smiles reaction

Indexed keywords

4 ISOCYANOPERMETHYLBUTANE 1,1,3 TRIOL; ALCOHOL DERIVATIVE; ALKANE DERIVATIVE; AMIDE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; FORMIC ACID; ISONITRILE DERIVATIVE; NUCLEOPHILE; PYRROLE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; SYNTHESIS;

EID: 84865690895     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.07.064     Document Type: Article

References (41)

1. J. Zhu, and H. Bienaymé Multicomponent Reactions 2005 Wiley-VCH Weinheim
2. A. Dömling, W. Wang, and K. Wang Chem. Rev. 112 2012 3083 3135
3. A. Dömling, and I. Ugi Angew. Chem., Int. Ed. 39 2000 3168 3210
4. S.S. van Berkel, B.G.M. Bögels, M.A. Wijdeven, B. Westermann, and F.P.J.T. Rutjes Eur. J. Org. Chem. 2012 3543 3559
5. C.R. Rhoden, D.G. Rivera, O. Kreye, A.K. Bauer, B. Westermann, and L.A. Wessjohann J. Comb. Chem. 11 2009 1078 1082
6. L.A. Wessjohann, D.G. Rivera, and O.E. Vercillo Chem. Rev. 109 2009 796 814
7. S. Brauch, M. Henze, B. Osswald, K. Naumann, L.A. Wessjohann, S.S. van Berkel, and B. Westermann Organic Biomol. Chem. 10 2012 958 965
8. A. Basso, L. Banfi, and R. Riva Eur. J. Org. Chem. 2010 1831 1841
9. C. Hulme, S. Chappeta, and J. Dietrich Tetrahedron Lett. 50 2009 4054 4057
10. C. Hulme, L. Ma, M.P. Cherrier, J.J. Romano, G. Morton, C. Duquenne, J. Salvino, and R. Labaudiniere Tetrahedron Lett. 41 2000 1883 1887
11. S. Marcaccini, and T. Torroba J. Zhu, H. Bienaymé, Multicomponent Reactions 2005 Wiley-VCH Weinheim 33 75
12. I. Akritopoulou-Zanze, and S.W. Djuric Heterocycles 73 2007 125 147
13. O. Kreye, B. Westermann, and L.A. Wessjohann Synlett 2007 3188 3192
14. T.A. Keating, and R.W. Armstrong J. Am. Chem. Soc. 117 1995 7842 7843
15. T.A. Keating, and R.W. Armstrong J. Am. Chem. Soc. 118 1996 2574 2583
16. C.B. Gilley, M.J. Buller, and Y. Kobayashi Org. Lett. 9 2007 3631 3634
17. C.B. Gilley, and Y. Kobayashi J. Org. Chem. 73 2008 4198 4204
18. T. Lindhorst, H. Bock, and I. Ugi Tetrahedron 55 1999 7411 7420
19. R.J. Linderman, S. Binet, and S.R. Petrich J. Org. Chem. 64 1999 336 337
20. A.L. Kennedy, A.M. Fryer, and J.A. Josey Org. Lett. 4 2002 1167 1170
21. K. Rikimaru, A. Yanagisawa, T. Kan, and T.A. Fukuyama Synlett 2004 41 43
22. M.C. Pirrung, and S. Ghorai J. Am. Chem. Soc. 128 2006 11772 11773
23. M.C. Pirrung, S. Ghorai, and T.R. Ibarra-Rivera J. Org. Chem. 74 2009 4110 4117
24. H.V. Le, L. Fan, and B.A. Ganem Tetrahedron Lett. 52 2011 2209 2211
25. E.E. Schultz, B.G. Pujanauski, and R. Sarpong Org. Lett. 14 2012 648 651
26. R.A. Neves Filho, B. Westermann, and L.A. Wessjohann Beilstein J. Org. Chem. 7 2011 1504 1507
27. O. Pando, S. Stark, A. Denkert, A. Porzel, R. Preusentanz, and L.A. Wessjohann J. Am. Chem. Soc. 133 2011 7692 7695
28. G.M. Chinigo, A. Breder, and E.M. Carreira Org. Lett. 13 2011 78 81
29. A. Plant, P. Thompson, and D.M. Williams J. Org. Chem. 74 2009 4870 4873
30. J. Isaacson, and Y. Kobayashi Angew., Chem. Int. Ed. 48 2009 1845 1848
31. J. Isaacson, M. Loo, and Y. Kobayashi Org. Lett. 10 2008 1461 1463
32. T. Maehara, R. Kanno, S. Yokoshima, and T. Fukuyama Org. Lett. 14 2012 1946 1948
33. A.M. Goldys, and C.S.P. McErlean Eur. J. Org. Chem. 2012 1877 1888
34. S.D. See, M.A. Brook, and T.H. Chan Tetrahedron Lett. 24 1983 1569 1572
35. D.A. Evans, G. Borg, and K.A. Scheidt Angew. Chem., Int. Ed. 41 2002 3188 3191
36. D.J. Dixon, M.S. Scott, and C.A. Luckhurst Synlett 2003 2317 2320
37. S. Matsunaga, T. Kinoshita, S. Okada, S. Harada, and M. Shibasaki J. Am. Chem. Soc. 126 2004 7559 7570
38. S. Chan, and T.F. Braish Tetrahedron 50 1994 9943 9950
39. S. Hanessian, U. Reinhold, and S. Ninkovic Tetrahedron Lett. 37 1996 8967 8970
40. S. Liu, and R.P. Hanzlik J. Med. Chem. 35 1992 1067 1075
41. X. Xie, X.Y. Lu, Y.Y. Liu, and W. Xu J. Org. Chem. 66 2001 6545 6550