Smiles cascades toward heterocyclic scaffolds

Organic Letters

Volumn 13, Issue 3, 2011, Pages 534-536

  El Kaim, Laurent ^a   Grimaud, Laurence ^a   Le Goff, Xavier F ^b   Schiltz, Aurélie ^a  

^a Ecole Nationale Superieure de Techniques Avancees   (France)

^b LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79851494840     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1028817     Document Type: Article

References (13)

1. (a) Levy, A. A.; Rains, H. C.; Smiles, S. J. Chem. Soc 1931, 3264. For reviews see:
2. (b) Bunnet, J. F.; Zaller, R. E. Chem. Rev. 1951, 49, 273-308.
3. (c) Truce, W. E.; Kreider, E. M.; Brand, W. W. Org. React. (N. Y.) 1970, 18, 99-215.
4. (d) Plesniak, K.; Zarecki, A.; Wicha, J. Top. Curr. Chem. 2007, 275, 163-250.
5. (a) Truce, W. E.; Ray, W. J., Jr.; Norman, O. L.; Eickemeyer, D. B. J. Am. Chem. Soc. 1958, 80, 3625-3629. For a review, see:
6. (b) Snape, T. J. Chem. Soc. Rev. 2008, 37, 2452-2458.
7. (a) El Kaim, L.; Grimaud, L.; Oble, J. Angew. Chem., Int. Ed. 2005, 44, 7165-7169.
8. El Kaim, L.; Gizolme, M.; Grimaud, L.; Oble, J. J. Org. Chem. 2007, 72, 4169-4180.
9. (a) El Kaim, L.; Gamez-Montaño, R.; Grimaud, L.; Ibarra-Rivera, T. Chem. Commun. 2008, 1350-1352.
10. (b) El Kaim, L.; Grimaud, L.; Wagschal, S. J. Org. Chem. 2010, 75, 5343-5346.
11. (a) For a possible Smiles rearrangement of N-aryl sulfonamide involving a three-membered spiro intermediate, see: Muller, P.; Phuong, N.-T. M. Helv. Chim. Acta 1979, 62, 494-496.
12. The crystallographic data can be obtained free of charge under the reference CCDC 801186 at the Cambridge Crystallographic Data Centre (www.ccdc.cam.ac.uk/data-request-cif).
13. A related Truce-Smiles rearrangement was already observed in a Ugi cyclic adduct (Dai, W.-M. Book of Abstracts, IV International Conference on Multi-component Reactions and Related Chemistry (MCR2009), Ekaterinburg, Russia, 24-28 May 2009, p 14).