Rhodium catalyzed allene amination: Diastereoselective synthesis of aminocyclopropanes via a 2-Amidoallylcation intermediate

Journal of the American Chemical Society

Volumn 132, Issue 7, 2010, Pages 2108-2109

  Stoll, Armin H ^a   Blakey, Simon B ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; DIASTEREOSELECTIVE SYNTHESIS; DIPOLAROPHILES; RHODIUM-CATALYZED; SULFAMATES;

ESTERS; RHODIUM;

CHEMICAL REACTIONS;

ALKYL GROUP; ALLENE DERIVATIVE; AMINOCYCLOPROPANE DERIVATIVE; BENZALDEHYDE; CYCLOPROPANE DERIVATIVE; DIRHODIUM TETRACARBOXYLATE; ELECTROPHILE; ENAMINE; ESTER DERIVATIVE; GRIGNARD REAGENT; HALIDE; HOMOALLENYLSULFAMATE ESTER; IMINE; IODINE; METAL DERIVATIVE; METALLONITRENE; METHANE; NITROGEN; NITRONE DERIVATIVE; NUCLEOPHILE; PIVALIC ACID; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RHODIUM DERIVATIVE; SOLVENT; TRIMETHYLENEMETHANE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

2 AMIDOALLYLCATION; ACYLATION; AMINATION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; CYCLOADDITION; EPOXIDATION; OXIDATION; RACEMIZATION; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 77950626751     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja908538t     Document Type: Article

References (38)

1. (a) Trost, B. M. Angew. Chem. 1986, 98, 1.
2. (b) Harmata, M. Adv. Cycloaddit. 1997, 4741.
3. (c) Harmata, M. Tetrahedron 1997, 35, 6235.
4. (d) Nakamura, E.; Yamago, S. Acc. Chem.. Res. 2002, 35, 867.
5. (e) Yamago, S.; Nakamura, E. Org. React. 2002, 61, 1.
6. (f) Hoffmann, H. M. R. Angew. Chem. 1984, 96, 29.
7. (a) Xiong, H.; Hsung, R. P.; Berry, C. R.; Rameshkumar, C. J. Am. Chem Soc. 2001, 123, 7174.
8. (b) Xiong, H.; Huang, J.; Ghosh, S. K. Hsung, R. P. J. Am. Chem. Soc. 2003, 125, 12694.
9. (c) Huang, J.; Hsung, R. P. J. Am. Chem. Soc. 2005, 127, 50.
10. (d) Wei, L.-L.; Xiong, H.; Hsung, R. P. Acc. Chem. Res. 2003, 36, 773.
11. (e) Harmata, M. Adv. Synth. Catal. 2006, 348, 2297.
12. (f) Harmata, M.; Huang, C.; Rooshenas, P.; Schreiner, P. R. Angew. Chem. Int. Ed. 2008, 47, 8696.
13. (g) Chung, W. K.; Lam, S. K.; Lo, B.; Liu, L. L.; Wong, W.-T.; Chiu, P. J. Am. Chem. Soc. 2009, 131, 4556.
14. (h) Lee, J. C.; Cha, J. K. J. Am. Chem. Soc. 2001, 123, 3243.
15. (i) Cho, S. Y.; Lee, H. I.; Cha, J. K. Org. Lett. 2001, 3, 2891.
16. (a) Crandall, J. K; Batal, D. J.; Lin, F.; Reix, T.; Nadol, G. S.; Ng, R. A. Tetrahedron 1992, 48, 1427.
17. (b) Crandall, J. K.; Rambo, E. Tetrahedron Lett. 1994, 35, 1489.
18. (c) Crandall, J. K.; Reix, T. Tetrahedron Lett. 1994, 35, 2513.
19. (d) Crandall, J. K.; Rambo, E. Tetrahedron 2002, 58, 7027.
20. (e) Katukojvala, S.; Barlett, K. N.; Lotesta, S. D.; Williams, L. J. J. Am. Chem. Soc. 2004, 126, 15348.
21. (f) Lotesta, S. D.; Kiren, S.; Sauers, R. R.; Williams, L. J. Angew. Chem. Int. Ed. 2007, 46, 7108.
22. (a)Tende, A. S.; Huang, H. Tetrahedron Lett. 1997, 38, 3353.
23. (b) Jin, S.-J.; Choi, J.-R.; Oh, J.; Lee, D.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 10914.
24. (c) Oh, J.; Lee, J.; Jin, S.-J.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3449.
25. Prie, G.; Prevost, N.; Twin, H.; Fernandes, S. A.; Hayes, J. F.; Shipman, M. Angew. Chem. Int. Ed. 2004, 43, 6517.
26. For lead references on the importance of aminocyclopropanes in biologically active natural products and drugs, see: (a) Gnad, F.; Reiser, O. Chem. Rev. 2003, 103, 1603.
27. (b) Burgess, K.-H.; Ho, K.-K.; Moye-Sherman, D. Synlett 1994, 575.
28. (c) Salaün, J. Top. Curr. Chem. 2000, 207, 1.
29. (d) Moreau, B.; Charette, A. B. J. Am. Chem. Soc. 2005, 127, 18014.
30. Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935.
31. (a) Thornton, A. R.; Blakey, S. B. J. Am. Chem. Soc. 2008, 130, 5020.
32. (b) Thornton, A. R.; Martin, V. I.; Blakey, S. B. J. Am. Chem. Soc. 2009, 131, 2434.
33. Espino, C. G.; Fiori, K. W.; Kim, M.; Du Bois, J. J. Am Chem. Soc. 2004, 126, 15378.
34. Stereochemistry determined by X-ray crystallography. See Supporting Information for details.
35. Piller, F. M.; Appukkuttan, P.; Gavryushin, A.; Helm, M.; Knochel, P. Angew. Chem., Int. Ed. 2008, 47, 6802.
36. Complete details of the solvents and oxidants investigated are included in the Supporting Information.
37. (a) Du Bois, J. Chemtracts-Org. Chem 2005, 18, 1.
38. (b) Bower, J. F.; Szeto, P.; Gallagher, T. Org. Lett. 2007, 9, 4909.