Can an aromatic ring alter the reactions of a nearby unsaturated imide? A study of the rate and selectivity of nitrile oxide cycloaddition reactions of acryloyl derivatives of the Rebek imide benzoxazole

Tetrahedron

Volumn 53, Issue 6, 1997, Pages 1971-1982

  Curran, Dennis P ^a   Yoon, Moon Hwan ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOXAZOLE DERIVATIVE; IMIDE;

ACYLATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0031562119     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)01167-2     Document Type: Article

References (19)

1. 1. a) Stack, J. G.; Curran, D. P.; Rebek, J., Jr.; Ballester, P. J. Am. Chem. Soc. 1991, 113, 5918.
2. b) Stack, J. G.; Curran, D. P.; Geib, S. V.; Rebek, J., Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007.
3. c) Jeong, K. S.; Paris, K.; Ballester, P.; Rebek, J., Jr. Angew. Chem. Int. Ed. 1990, 29-55.
4. 2. Seyden-Penne, J. "Chiral Auxiliaries, Ligands and Catalysts" Wiley Interscience: NY; 1996.
5. 3. Jones, G. B.; Chapman, B. J. Synthesis 1995, 475.
6. 4. For example, see: Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem. Int. Ed. 1995, 34, 1059.
7. 5. a) Maddaluno, J. F.; Gresh, N.; Giessnerprettre, C. J. Org. Chem. 1994, 59, 793.
8. b) Dumas, F.; Mezrhab, B.; d'Angelo, J.; Riche, C.; Chiaroni, A. J. Org. Chem. 1996, 61, 2293.
9. 6. Nitrile oxide cycloadditions: a) Kirn, B. H.; Curran, D. P. Tetrahedron 1993, 49, 293.
10. b) Kanemasa, S.; Onimura, K.; Wada, E.; Tanaka, J. Tetrahedron-Asymmetry 1991, 2, 1185.
11. c) Kanemasa, S.; Onimura, K. Tetrahedron 1992, 48, 8631.
12. d) Kanemasa, S.; Onimura, K. Tetrahedron 1992, 48, 8645.
13. 7. Radical additions: a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications; VCH: Weinheim, 1996.
14. b) Sibi, M. P.; Jasperse, C. P.; Ji, J. G. J. Am. Chem. Soc. 1995, 117, 10779.
15. 8. Caramella, P.; Grünanger, P. "1,3-Dipolar Cycloaddition Chemistry." Padwa, A., Ed.; Wiley: NY 1984, Vol. 1,p. 291.
16. 9. Qi, H. Ph.D. Thesis. University of Pittsburgh, 1995.
17. 10. These groups are anti in the one available X-ray structure (an imide that was used to resolve the benzoxazole). See reference 1b.
18. 11. Curran, D. P.; Heffner, T. A. J. Org. Chem. 1990, 55, 4585.
19. 12. That the sorboyl derivatives gave a 2/1 ratio tentatively suggests that the low stereoisomer ratio in this case is due to reaction from one face through s-cis and s-trans conformers. Reactions from both faces of 4f would be expected to give a 1/1 raw ratio of products in the competition experiment.