Xanthene-4,5-diamine derivatives: A study of anion-binding catalysis

Tetrahedron Letters

Volumn 56, Issue 37, 2015, Pages 5180-5184

  Metz, Alison E ^a   Ramalingam, Kailasham ^a   Kozlowski, Marisa C ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

Anion binding catalyst; Asymmetric organocatalysis; Furan cyclization; N acyliminium ions; Xanthene 4,5 diamine

Indexed keywords

ACRIDONE DERIVATIVE; ANION; DIAMINE DERIVATIVE; FURAN DERIVATIVE; XANTHENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; ENANTIOSELECTIVITY; HYDROGEN BOND; SYNTHESIS;

EID: 84938867392     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2015.07.058     Document Type: Article

References (32)

1. J. Lacour, and D. Moraleda Chem. Commun. 2009 7073 7089
2. R.J. Phipps, G.L. Hamilton, and F.D. Toste Nat. Chem. 4 2012 603 614
3. K. Brak, and E.N. Jacobsen Angew. Chem., Int. Ed. 52 2013 534 561
4. M. Mahlau, and B. List Angew. Chem., Int. Ed. 52 2013 518 533
5. Z.G. Zhang, and P.R. Schreiner Chem. Soc. Rev. 38 2009 1187 1198
6. A. Moyano, and R. Rios Chem. Rev. 111 2011 4703 4832
7. J. Brière, S. Oudeyer, V. Dalla, and V. Levacher Chem. Soc. Rev. 41 2012 1696 1707
8. C.K. De, N. Mittal, and D.A. Seidel J. Am. Chem. Soc. 133 2011 16802 16805
9. I.T. Raheem, P.S. Thiara, E.A. Peterson, and E.N. Jacobsen J. Am. Chem. Soc. 129 2007 13404 13405
10. E.A. Peterson, and E.N. Jacobsen Angew. Chem., Int. Ed. 48 2009 6328 6331
11. I.T. Raheem, P.S. Thiara, and E.N. Jacobsen Org. Lett. 10 2008 1577 1580
12. F.P. Schmidtchen, and M. Berger Chem. Rev. 97 1997 1609 1646
13. S.E. García-Garido, C. Caltagirone, M.E. Light, and P.A. Gale Chem. Commun. 2007 1450 1452
14. P. Bühlmann, S. Nishizawa, K.P. Xiao, and Y. Umezawa Tetrahedron 53 1997 1647 1654
15. T. Nemoto, K. Obuchi, S. Tamura, T. Fukuyama, and Y. Hamada Tetrahedron Lett. 52 2011 987 991
16. H. Hanawa, S. Kii, and K. Maruoka Adv. Synth. Catal. 343 2001 57 60
17. G. Malaisé, L. Barloy, and J.A. Osborn Tetrahedron Lett. 42 2001 7417 7419
18. R. Rasappan, D. Laventine, and O. Reiser Coord. Chem. Rev. 252 2008 702 714
19. F.G. Bordwell, H.E. Fried, D.L. Hughes, T.Y. Lynch, A.V. Satish, and Y.E. Whang J. Org. Chem. 55 1990 3330 3336
20. N.J. Andrews, C.J.E. Haynes, M.E. Light, S.J. Moore, C.C. Tong, J.T. Davis, W.A. Harrell, and P.A. Gale Chem. Sci. 2 2011 256 260
21. G. Jakab, C. Tancon, Z. Zhang, K.M. Lippert, and P.R. Schreiner Org. Lett. 14 2012 1724 1727
22. R.C. Jagessar, M. Shang, W.R. Scheidt, and D.H. Burns J. Am. Chem. Soc. 120 1998 11684 11692
23. N.H. Evans, and P.D. Beer Angew. Chem., Int. Ed. 53 2014 11716 11754
24. P.A. Gale, N. Busschaert, C.J.E. Haynes, L.E. Karagiannidis, and I.L. Kirby Chem. Soc. Rev. 43 2014 205 241
25. M.J. Chmielewski, and J. Jurczak Chem. Eur. J. 11 2005 6080 6094
26. S.P. Tanis, M.V. Deaton, L.A. Dixon, M.C. McMills, J.W. Raggon, and M.A. Collins J. Org. Chem. 63 1998 6914 6928
27. H. Huang, X. Ji, W. Wu, and H. Jiang Chem. Commun. 2013 3351 3353
28. M.J. Frisch, and et al. Gaussian 09, rev performed using GAUSSIAN09, revision A.02 2009 Gaussian Wallington CT Additional details can be found in the Supporting information
29. J.J. Maresh, L.-A. Giddings, A. Friedrich, E.A. Loris, S. Panjikar, B.L. Trout, J. Stockigt, B. Peters, and S.E. O'Connor J. Am. Chem. Soc. 130 2008 710 723
30. E.V. Ansyln, and D.A. Dougherty Molecular Structure and Thermodynamics: Introduction to Structure and Models of Bonding Modern Physical Organic Chemistry 2006 University of Sciences Books California 146
31. Greener Solvent Alternatives: Supporting the Advancement of Chemistry through Sounds Environmental, Social & Fiscal Responsibilities. 2010, Sigma-Aldrich Co. https://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Sigma/Brochure/greener-solvent-alternatives.pdf. (accessed March 31, 2015).
32. L. Marcheselli, G. Pistoni, M. Tagliazucchi, L. Tassi, and G. Tosi J. Chem. Eng. Data 38 1993 204 206