Base-Promoted Reactions of Bridged Ketones and 1,3- and 1,4-Haloalkyl Azides: Competitive Alkylation vs Azidation Reactions of Ketone Enolates

Journal of Organic Chemistry

Volumn 69, Issue 5, 2004, Pages 1720-1722

  Yao, Lei ^a   Smith, Brenton T ^a   Aubé, Jeffrey ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; AROMATIC COMPOUNDS; SYNTHESIS (CHEMICAL);

BASE-PROMOTED REACTIONS; INITIAL AZYDATION;

KETONES;

2 NORBORNANONE; ALKYL GROUP; AZIDE; HALIDE; KETONE DERIVATIVE; KETONE ENOLATE; NORBORNANE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; AZIDATION; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS;

ALKYLATION; AZIDES; BRIDGED COMPOUNDS; HYDROCARBONS, HALOGENATED; KETONES; MOLECULAR STRUCTURE;

EID: 1442275449     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0356098     Document Type: Article

References (36)

1. (a) Krieger, H.; Sodervall, M. Suom. Kemistil. B 1967, 40, 294-297.
2. (b) Olsen, C. E.; Pedersen, C. Tetrahedron Lett. 1968, 3805-3809.
3. (c) Olsen, C. E.; Pedersen, C. Acta Chem. Scand. 1973, 27, 2279-2286.
4. (d) Olsen, C. E. Acta Chem. Scand. 1973, 27, 2989-2996.
5. (e) Olsen, C. E. Acta Chem. Scand. 1973, 27, 1987-2000.
6. (f) Olsen, C. E.; Pedersen, C. Acta Chem. Scand. 1973, 27, 2271-2278.
7. (g) Olsen, C. E. Acta Chem. Scand. 1973, 27, 2983-2988.
8. (h) Olsen, C. E. Angew. Chem., Int. Ed. Engl. 1974, 13, 349.
9. (i) Olsen, C. E. Acta Chem. Scand., Ser. B: Org. Chem. Biochem. 1974, 28, 425-432.
10. (j) Olsen, C. E. Acta Chem. Scand., Ser. B: Org. Chem. Biochem. 1975, B29, 953-962.
11. (k) Babudri, F.; Di Nunno, L.; Florio, S.; Valzano, S. Tetrahedron 1984, 40, 1731-1736.
12. (l) Di Nunno, L.; Scilimati, A. Tetrahedron 1986, 42, 3913-3929.
13. (m) Ognyanov, V. I.; Hesse, M. Helv. Chim. Acta 1991, 74, 899-903.
14. (a) Azadi-Ardakani, M.; Alkhader, M. A.; Lippiatt, J. H.; Patel, D. I.; Smalley, R. K.; Higson, S. J. Chem. Soc., Perkin Trans. 1 1986, 1107-1111.
15. (b) Pearson, W. H.; Mi, Y.; Lee, I. Y.; Stoy, P. J. Am. Chem. Soc. 2001, 123, 6724-6725.
16. (a) Evans, D. A.; Britton, T. C. J. Am. Chem. Soc. 1987, 109, 6881-6883.
17. (b) Evans, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1989, 111, 1063-1072.
18. (c) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011-4030.
19. (d) Evans, D. A.; Evrard, D. A.; Rychnovsky, S. D.; Früh, T.; Whittingham, W. G.; DeVries, K. M. Tetrahedron Lett. 1992, 33, 1189-1192.
20. (e) Stone, M. J.; Maplestone, R. A.; Rahman, S. K.; Williams, D. H. Tetrahedron Lett. 1992, 32, 2663-2666.
21. (f) Boteju, L. W.; Wegner, K.; Qian, X.; Hruby, V. J. Tetrahedron 1994, 50, 2391-2404.
22. (g) Chung, K.-H.; An, S.-O. J. Korean Chem. Soc. 1995, 39, 431-433.
23. (h) Kumar, J. S. D.; Dupradeau, F.-Y.; Strouse, M. J.; Phelps, M. E.; Toyokuni, T. J. Org. Chem. 2001, 66, 3220-3223.
24. (a) Wendt, J. A.; Aubé, J. Tetrahedron Lett. 1996, 37, 1531-1534.
25. (b) Smith, B. T.; Wendt, J. A.; Aubé, J. Org. Lett. 2002, 4, 2577-2579.
26. Gassman, P. G.; Burns, S. J.; Pfister, K. B. J. Org. Chem. 1993, 58, 1449-1457.
27. Similarly, reaction of the TMS enol ether of 2-norbornanone with benzyl azide did not result in any 1,2,3-triazoline when reacted at room temperature for the 2 h required for the conversion of the enolate of 2-norbornanone to compound 10 (see Scheme 4). However, heating of these reactants at 60 °C for 2 days afforded the same product in high yield: Auberson, Y.; Vogel, P. Tetrahedron 1990, 46, 7019-7032.
28. Another possibility, not shown, is that the conversion of the enolate to the alkoxide intermediate involves a direct [3+2] cyclo-addition of the alkyl azide onto the enolate. We have no evidence to either support or exclude such a possibility at the present time.
29. (a) Hall, J. H.; Behr, F. E.; Reed, R. L. J. Am. Chem. Soc. 1972, 94, 4952-4958.
30. (b) Sha, C.-K.; Ouyang, S.-L.; Hsieh, D.-Y.; Hseu, T. H. J. Chem. Soc., Chem. Commun. 1984, 492-494.
31. (c) Sha, C.-K.; Ouyang, S.-L.; Hsieh, D.-Y.; Chang, R.-C.; Chang, S.-C. J. Org. Chem. 1986, 51, 1490-1494.
32. (d) Wender, P. A.; Cooper, C. B. Tetrahedron Lett. 1987, 28, 6125-6128.
33. (e) Benati, L.; Montevecchi, P. C.; Spagnolo, P.; Foresti, E. J. Chem. Soc., Perkin Trans. 1 1992, 2845-2850.
34. (f) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
35. (g) Rozin, Y. A.; Savel'eva, E. A.; Morzherin, Y. Y.; Dehaen, W.; Toppet, S.; Van Meervelt, L.; Bakulev, V. A. J. Chem. Soc., Perkin Trans. 1 2002, 211-216.
36. (h) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193.