Synthesis, structural analysis, and reactivity of bridged orthoamides by intramolecular schmidt reaction

Journal of the American Chemical Society

Volumn 132, Issue 8, 2010, Pages 2530-2531

  Szostak, Michal ^a   Aubé, Jeffrey ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EN-ROUTE; HETEROCYCLES; HIGH YIELD; SYSTEMATIC STUDY; TETRAHEDRAL INTERMEDIATES;

ADDITION REACTIONS; AMIDES; REACTION INTERMEDIATES; REGIOSELECTIVITY; STRUCTURAL ANALYSIS;

SYNTHESIS (CHEMICAL);

ACETAL; AMIDE; AZIDE; CYCLOHEXANONE; KETONE; HETEROCYCLIC COMPOUND;

ADDITION REACTION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; SCHMIDT REACTION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; X RAY ANALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMIDES; HETEROCYCLIC COMPOUNDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 77950406176     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja910654t     Document Type: Article

References (20)

1. For recent reviews, see: (a) Nyfeler, E.; Renaud, P. Chimia 2006, 60, 276-284.
2. (b) Lang, S.; Murphy, J. A. Chem. Soc. Rev. 2006, 35, 146-156.
3. (c) Grecian, S.; Aube, J., Organic Azides: Syntheses and Applications; Bräse, S., Banert, K., Eds.; John Wiley and Sons: 2009.
4. (a) Yao, L.; Aubé, J. J. Am. Chem. Soc. 2007, 129, 2766-2767.
5. (b) Szostak, M.; Yao, L.; Aubé, J. Org. Lett. 2009, 11, 4386-4389.
6. For recent reviews, see: (a) Greenberg, A., Breneman, C. M.; Liebman, J. F. Amide Linkage: Selected Structural Aspects in. Chemistry, Biochemistry, and Materials Science; Wiley: New York, 2000.
7. (b) Clayden, J.; Moran, W. J. Angew. Chem., Int. Ed. 2006, 45, 7118-7120.
8. For selected examples, see: (c) Kirby, A. J.; Komarov, I. V.; Feeder, N. J. Chem. Soc., Perkin Trans. 2 2001, 522-529.
9. (d) Tani, K.; Stoltz, B. M. Nature 2006, 441, 731-734.
10. (e) Lei, Y.; Wrobleski, A. D.; Golden, J. E.; Powell, D. R.; Aubé, J. J. Am. Chem. Soc. 2005, 127, 4552-4553.
11. (a) Adler, M.; Adler, S.; Boche, G. J. Phys. Org. Chem. 2005, 18, 193-209.
12. (b) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: 1983.
13. (c) Evans, D. A.; Borg, G.; Scheidt, K. A. Angew. Chem., Int. Ed. 2002, 41, 3188-3191.
14. (d) Kirby, A. J.; Komarov, T. V.; Feeder, N. J. Am. Chem. Soc. 1998, 120, 7101-7102.
15. (e) Szostak, M.; Aubé, J. J. Am. Chem. Soc. 2009, 151, 13246-13247.
16. (a) Mossman, C. J.; Aubé, J. Tetrahedron 1996, 52, 3403-3408.
17. (b) Iyengar, R.; Schildknegt, K.; Morton, M.; Aubé, J. Org. Chem. 2005, 70, 10645-10652.
18. (c) Milligan, G. L.; Mossman, C. J.; Aubé, J. J. Am. Chem. Soc. 1995, 117, 10449-10459.
19. 1H NMR. See SI for details.
20. Lactam 2n was originally reported in ref 5a as a fused isomer. We now reassign 2n as a bridged orthoamide. See SI for details.