Tandem formation and [2,3] rearrangement of methylene ammonium ylides derived from amines and the Simmons-Smith reagent

Organic Letters

Volumn 5, Issue 10, 2003, Pages 1757-1760

  Aggarwal, Varinder K ^a   Fang, Guang Yu ^a   Charmant, Jonathan P H ^a   Meek, Graham ^b  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b DOW CHEMICAL COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AMMONIUM DERIVATIVE; LITHIUM DERIVATIVE; OXAZOLIDINE DERIVATIVE; REAGENT; SIMMONS SMITH REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DIASTEREOISOMER; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; REACTION ANALYSIS; SIMMONS SMITH REACTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0141852823     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034404i     Document Type: Article

References (34)

1. Wittig, G.; Schwarzenbach, K. Liebigs Ann. Chem. 1961, 650, 1.
2. For a review on ammonium ylide, see: Markó, I. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Elmsford, NY, 1991; p 913. For a recent review on asymmetric ylide chemistry, see: Aggarwal, V. K.; Li, A. H.; Dai, L. X. Chem. Rev. 1997, 97, 2341.
3. For a review on ammonium ylide, see: Markó, I. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Elmsford, NY, 1991; p 913. For a recent review on asymmetric ylide chemistry, see: Aggarwal, V. K.; Li, A. H.; Dai, L. X. Chem. Rev. 1997, 97, 2341.
4. Vedejs, E.; West, F. G. Chem. Rev. 1986, 86, 941.
5. Maeda, Y.; Sato, Y. J. Org. Chem. 1996, 61, 5188.
6. Stevens, T. S.; Creighton, E. M.; Gordon, A. B.; Macnicol, M. J. Chem. Soc. 1928, 3193.
7. Meada, Y.; Sato, Y. J. Chem. Soc., Perkin Trans. 1 1997, 1491.
8. (a) Furukara, J.; Kawabata, N.; Nishimura, J. Tetrahedron Lett. 1968, 3495.
9. (b) Furukara, J.; Kawabata, N.; Nishimura, J. Tetrahedron 1969, 25, 2647.
10. Allylic amines bearing a non-nucleophilic nitrogen readily undergo cyclopropanation with the Simmons-Smith reagent; see: Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2003, 125, 761.
11. (a) Kozarych, Z.; Cohen, T. Tetrahedron Lett. 1982, 23, 3019.
12. (b) Charette, A. B.; Marcoux, J. F.; Molinaro, C.; Beauchemin, A.; Brochu, C.; Isabel, E. J. Am. Chem. Soc. 2000, 122, 4508.
13. (a) Aggarwal, V. K.; Ali, A.; Coogan, M. P. J. Org. Chem. 1997, 62, 8628.
14. (b) Aggarwal, V. K.; Coogan, M. P.; Stenson, R. A.; Jones, R. V. H; Fieldhouse, R.; Blacker, J. Eur. J. Org. Chem. 2002, 2, 319.
15. Aggarwal, V. K.; Stenson, R. A.; Jones, R. V. H.; Fieldhouse, R.; Blacker, J. Tetrahedron Lett. 2001, 42, 1587.
16. 2Ph are 30.8 and 18.8, respectively: Cheng, J. P.; Liu, B; Zhao, Y. Y.; Sun, Y.; Zhang, X; Lu, Y. J. Org. Chem. 1999, 64, 604.
17. We have tried MeONa and pseudo-ephedrine salts made from 1 equiv of (1R,2R)-pseudo-ephedrine/1 equiv of LiHMDS or NaHMDS and 1 equiv of (1R,2R)-pseudo-ephendrine/2 equiv of n-BuLi as additives in THF solution at 0°C. In all cases, no neutral amines were obtained after workup.
18. Sommelet, M.; Hauser, C. R. Hebd. Seances Acad. Sci. 1937, 205, 56.
19. (a) Khruscheva, N. S.; Loim, N. M.; Sokolov, V. L.; Makhaev, V. D. J. Chem. Soc., Perkin Trans. 1 1997, 2425.
20. (b) Huche, M.; Aubouet, J.; Pourcelot, G.; Berlan, J. Tetrahedron Lett. 1983, 24, 585.
21. (c) Hassan, A.; Rene, G.; Robert, C. Tetrahedron Lett. 1982, 23, 503.
22. (d) Mangeney, P.; Alexakis, A.; Normant, J. F. Tetrahedron, 1984, 40, 1803.
23. Hussain, A.; Wyatt, P. B. Tetrahedron 1993, 49, 2123.
24. Glaeske, K. V.; West, F. G. Org. Lett. 1999, 1, 31.
25. For other examples of rearrangements of ammonium ylides to give eight-membered rings, see: (a) Clark, J. S.; Hodgson, P. B. Tetrahedron Lett. 1995, 36, 2519. (b) Wright, D. L.; Weekly, R. M.; Groff, R.; McMills, M. C. Tetrahedron Lett. 1996, 37, 2165. (c) Vedejs, E.; Hagen, J. P.; Roach, B. L.; Spear, K. L. J. Org. Chem. 1978, 43, 1185.
26. For other examples of rearrangements of ammonium ylides to give eight-membered rings, see: (a) Clark, J. S.; Hodgson, P. B. Tetrahedron Lett. 1995, 36, 2519. (b) Wright, D. L.; Weekly, R. M.; Groff, R.; McMills, M. C. Tetrahedron Lett. 1996, 37, 2165. (c) Vedejs, E.; Hagen, J. P.; Roach, B. L.; Spear, K. L. J. Org. Chem. 1978, 43, 1185.
27. For other examples of rearrangements of ammonium ylides to give eight-membered rings, see: (a) Clark, J. S.; Hodgson, P. B. Tetrahedron Lett. 1995, 36, 2519. (b) Wright, D. L.; Weekly, R. M.; Groff, R.; McMills, M. C. Tetrahedron Lett. 1996, 37, 2165. (c) Vedejs, E.; Hagen, J. P.; Roach, B. L.; Spear, K. L. J. Org. Chem. 1978, 43, 1185.
28. For another example in which one diastereoisomer of an ylide undergoes [2,3] rearrangement and the other diastereomer undergoes a [1,2] rearrangement, see ref 18b.
29. Ylide 15 would not be expected to undergo Stevens rearrangement, as [2,3] sigmatropic rearrangements are generally faster processes than [1,2] rearrangements. Mageswaran, S.; Ollis, W. D.; Sutherland, I. O.; Thebtaranonth, Y. J. Chem. Soc., Chem. Commun. 1971, 1494. For a review on Stevens rearrangements, see ref 2.
30. (a) Chelucci, G.; Saba, A.; Valenti, R.; Bacchi, A. Tetrahedron: Asymmetry 2000, 11, 3449.
31. (b) Naidu, B. N.; West, F. G. J. Am. Chem. Soc. 1994, 116, 8520.
32. For other examples of ylides derived from acetals/thioacetals undergoing effectively a [1,2] rearrangement, see: (a) Doyle, M. P.; Griffin, J. H.; Chinn, M. S.; Leusen, D. V. J. Org. Chem. 1984, 49, 1917. (b) Trauner, D.; Porth, S.; Opatz, T.; Bats, J. W.; Giester, G.; Mülzer, J. Synthesis 1998, 653. (c) Mülzer, J.; Trauner, D.; Bats, J. W. Angew. Chem., Int. Ed. Engl. 1996, 35, 1970.
33. For other examples of ylides derived from acetals/thioacetals undergoing effectively a [1,2] rearrangement, see: (a) Doyle, M. P.; Griffin, J. H.; Chinn, M. S.; Leusen, D. V. J. Org. Chem. 1984, 49, 1917. (b) Trauner, D.; Porth, S.; Opatz, T.; Bats, J. W.; Giester, G.; Mülzer, J. Synthesis 1998, 653. (c) Mülzer, J.; Trauner, D.; Bats, J. W. Angew. Chem., Int. Ed. Engl. 1996, 35, 1970.
34. For other examples of ylides derived from acetals/thioacetals undergoing effectively a [1,2] rearrangement, see: (a) Doyle, M. P.; Griffin, J. H.; Chinn, M. S.; Leusen, D. V. J. Org. Chem. 1984, 49, 1917. (b) Trauner, D.; Porth, S.; Opatz, T.; Bats, J. W.; Giester, G.; Mülzer, J. Synthesis 1998, 653. (c) Mülzer, J.; Trauner, D.; Bats, J. W. Angew. Chem., Int. Ed. Engl. 1996, 35, 1970.