Metal-free highly regioselective aminotrifluoroacetoxylation of alkenes

Journal of the American Chemical Society

Volumn 132, Issue 4, 2010, Pages 1249-1251

  Lovick, Helena M ^a   Michael, Forrest E ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZEPANES; CHEMICAL EQUATIONS; COUNTERIONS; CYCLIZED PRODUCTS; DIASTEREOSELECTIVITIES; FUNCTIONALIZED; HYPERVALENT IODINE; MULTIPLE RING; NITROGEN-CONTAINING HETEROCYCLES; OXIDATIVE CYCLIZATION; PYRROLIDINES; REGIO-SELECTIVE; RING CLOSURES; SUBSTITUTION PATTERNS;

ACIDS; AMIDES; IODINE; OLEFINS; REGIOSELECTIVITY; SULFUR COMPOUNDS;

CYCLIZATION;

ALKENE; HETEROCYCLIC COMPOUND; IODINE; PIPERIDINE DERIVATIVE; SULFONAMIDE; TRIFLUOROACETIC ACID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; GEOMETRY; HYDROXYLATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 77950445785     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja906648w     Document Type: Article

References (47)

1. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev 1994, 94, 2483-2547.
2. (a) Bodkin, J. A.; McLeod, M. D. J. Chem. Soc., Perkin Trans. 1 2002, 2733-2746.
3. (b) O'Brien, P. Angew. Chem., Int. Ed. 1999, 38 (3), 326-329.
4. (a) Wirth, T. Angew. Chem., Int. Ed. 2005, 44, 3656-3665.
5. (b) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584.
6. (c) Deprez, N. R.; Sanford, M. S. Inorg. Chem. 2007, 46, 1924-1935.
7. (d) Prakash, O.; Saini, N.; Sharma, P. K. Synlett 1994, 221-227.
8. (e) Moriearty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244-250.
9. (a) Liu, G.; Stahl, S. S. J. Am. Chem. Soc. 2006, 128, 7179-7181.
10. (b) Li, Y.; Song, D.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 2962-2964.
11. (c) Muñiz, K.; Hövelmann, C. H.; Streuff, J. J. Am. Chem. Soc. 2008, 130, 763-773.
12. (a) Emmanuvel, L.; Shaikh, T. M. A.; Sudalai, A. Org. Lett. 2005, 7, 5071-5074.
13. (b) Zefirov, N. S.; Zhdankin, V. V.; Dan'kov, Y. V.; Sorokin, V. D.; Semerikov, V. N.; Koz'min, A. S.; Caple, R.; Berglund, B. A. Tetrahedron Lett. 1986, 27, 3971-2974.
14. (a) Donohoe, T. J.; Winship, P. C. M.; Walter, D. S. J. Org. Chem. 2009, 74, 6394.
15. (b) Donohoe, T. J.; Callens, C. K. A.; Thompson, A. L. Org. Lett. 2009, 11, 2305-2307.
16. (c) Donohoe, T. J.; Johnson, P. D.; Pye, R. J.; Keenan, M. Org. Lett. 2004, 6, 2583-2585.
17. Alexanian, E. J.; Lee, C.; Sorensen, E. J. J. Am. Chem. Soc. 2005, 127, 7690-7691.
18. Cochran, B. M.; Michael, F. E. Org. Lett. 2008, 10, 5039-5042.
19. (a) Exo selective, oxidative aminohydroxylations: Tellitu, I.; Urrejola, A.; Serna, S.; Moreno, I.; Herrero, M. T.; Domínguez, E.; SanMartin, R.; Correa, A. Eur. J. Org. Chem. 2007, 437-444.
20. (b) Minakata, S.; Kano, D.; Oderaotoshi, Y.; Komatsu, M. Org. Lett. 2002, 4, 2097-2099.
21. (c) Serna, S.; Tellitu, I.; Domínguez, E.; Moreno, I.; SanMartin, R. Tetrahedron 2004, 60, 6533-6539.
22. (d) Davis, F. A.; Song, M.; Augustine, A. J. Org. Chem. 2006, 71, 2779-2786.
23. (e) Morino, Y.; Hidaka, I.; Oderaotoshi, Y.; Komatsu, M.; Minakata, S. Tetrahedron 2006, 62, 12247-12251.
24. Following submission of this manuscript for publication, related work by Wardrop and coworkers was published in this journal: Wardrop, D. J.; Bowen, E. G.; Forslund, R. E.; Sussman, A. D.; Weerasekera, S. L. J. Am. Chem. Soc. 2009, ASAP (DOI: 10.1021/ja9069997).
25. Some hydrolysis of the trifluoroacetates was observed upon standing. Therefore, the aminotrifluoroacetoxylation products were intentionally saponified to the aminoalcohols during isolation.
26. Kokotos, C. G.; Aggarwal, V. K. Chem. Commun. 2006, 2156-2158.
27. Cyclizaton of E-14 also gave a mixture of regioisomers.
28. Some cis/trans isomerism was observed in the presence of acid alone.
29. When the iodoamination is performed with NIS, only the 5-exo pyrrolidine product is observed.
30. (a) Li, Z.; Ding, X.; He, C. J. Org. Chem. 2006, 71, 5876-5880.
31. (b) Liu, P.; Wong, E. L.-M.; Wing-Hoi, A.; Che, C.-M. Org. Lett. 2008, 10, 3275-3278.
32. (c) Fan, R.; Pu, D.; Gan, J.; Wang, B. Tetrahedron Lett. 2008, 49, 4925-4928.
33. (d) Xu, Q.; Appella, D. H. Org. Lett. 2008, 10, 1497-1500.
34. (a) Krow, G. R.; Gandla, D.; Gu, W.; Centafont, R. A.; Lin, G.; DeBrosse, C.; Sonnet, P. E.; Ross, C. W., III; Ramjit, H. G.; Carroll, P. J.; Cannon, K. C. J. Org. Chem. 2008, 73, 2114-2121.
35. (b) Cossy, J.; Dumas, C.; Pardo, D. G. Synlett 1997, 905-906.
36. (c) Padwa, A.; Stengel, T. Org. Lett. 2002, 4, 2137-2139.
37. (d) Ori, M.; Toda, N.; Takami, K.; Tago, K.; Kogen, H. Angew. Chem., Int. Ed. 2003, 42, 2540-2543.
38. A related mechanism invoking the formation of an oxonium ion has been proposed. Kim, H.-J.; Schlecht, M. F. Tetrahedron Lett. 1987, 28, 5229-5232.
39. (a) Löfstedt, J.; Pettersson-Fasth, H.; Bäckvall, J.-E. Tetrahedron 2000, 56, 2225-2230.
40. (b) Moody, C. J.; Lightfoot, A. P.; Gallaher, P. T. J. Org. Chem. 1997, 62, 746-748.
41. (c) Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796.
42. (d) Hedley, S. J.; Moran, W. J.; Prenzel, A. H. G. P.; Price, D. A.; Harrity, J. P. A. Synlett 2001, 10, 1596-1598.
43. (e) Harding, K. E.; Burks, S. R. J. Org. Chem. 1984, 49, 40-44.
44. (f) Hirai, Y.; Shibuya, K.; Fukuda, Y.; Yokoyama, H.; Yamaguchi, S. Chem. Lett. 1997, 221-222.
45. (g) Fry, D. F.; Brown, M.; McDonald, J. C. Tetrahedron Lett. 1996, 37, 6227-6230.
46. (a) Bisai, A.; Singh, V. K. Tetrahedron Lett. 2007, 48, 1907-1910.
47. (b) Oka, T.; Yasusa, T.; Ando, T.; Wantanabe, M.; Yoneda, F.; Ishida, T.; Knoll, J. Bioorg. Med. Chem. 2001, 9, 1213-1219.