Exo Selective Enantioselective Nitrone Cycloadditions

Journal of the American Chemical Society

Volumn 126, Issue 3, 2004, Pages 718-719

  Sibi, Mukund P ^a   Ma, Zhihua ^a   Jasperse, Craig P ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LEWIS ACID; NITRONE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLOADDITION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY;

EID: 1642535360     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja039087p     Document Type: Article

References (26)

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2. (b) Gothelf, K. V.; Jørgensen, K. A. Chem. Commun. 2000, 1449.
3. (c) Kanemasa, S. Synlett 2002, 1371.
4. (d) Confalone, P. N.; Hule, E. M. Org. React. 1988, 1.
5. (a) Kanemasa, S.; Oderaotoshi, Y.; Tanaka, J.; Wada, E. J. Am. Chem. Soc. 1998, 120, 12355.
6. (b) Karlsson, S.; Hogberg, H.-E. Tetrahedron: Asymmetry 2002, 13, 923.
7. (c) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874.
8. (d) Kobayashi, S.; Kawamura, M. J. Am. Chem. Soc. 1998, 120, 5840.
9. (e) Iwas, S.; Tsushima, S.; Shimada, T.; Nishiyama, H. Tetrahedron 2002, 58, 227.
10. (f) Desimoni, G.; Falta, G.; Mortoni, A.; Righetti, P. Tetrahedron Lett. 1999, 40, 2001.
11. For a discussion, see: Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1996, 61, 346.
12. (b) Gothelf, K. V.; Jørgensen, K. A. J. Org. Chem. 1994, 59, 5687.
13. (c) Crosignani, S.; Desimoni, G.; Fiata, G.; Filippone, S.; Mortoni, A.; Righeti, P. P.; Zema, M. Tetrahedron Lett. 1999, 40, 7007.
14. (d) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017.
15. (e) Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1998, 63, 5483.
16. For reactions proceeding with good exo diasloreoselectivity or enantioselectivity, see: (a) Jensen, K. B.; Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1997, 62, 2471.
17. Achiral templates with fluxional groups in synthesis, see: (a) Sibi, M. P.; Venkatraman, L.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 2001, 123, 8444.
18. (b) Corminboeuf, O.; Quaranta, L.; Renaud, P.; Liu, M.; Jasperse, C. P.; Sibi, M. P. Chem.-Eur. J. 2003, 9, 28.
19. (c) Sibi, M. P.; Liu, M. Org. Lett. 2001, 3, 4181.
20. See Supporting Information for details on the synthesis of the starting materials, nitrones, stereochemistry analysis, and experimental conditions.
21. The identities of the exo and endo adducts were established by converting them to known compounds. See Supporting Information for details.
22. Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 35, 325.
23. (a) References 2a, 4a, and 4c.
24. (b) Kawamura, M.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 3213.
25. These results suggest that there may be competing pathways when MS are added. The high enantioselectivity for the exo adduct with or without MS suggests that it may be formed without the involvement of the sieves.
26. This conclusion is consistent with the high exo selectivity with copper as a Lewis acid (square planar complex) rather than magnesium or iron Lewis acids (typically letrahedral or octahedral geometry).