Oxidatively generated electrophiles as initiators of epoxide cascade cyclization processes

Tetrahedron Asymmetry

Volumn 16, Issue 21, 2005, Pages 3570-3578

  Kumar, V Satish ^a   Wan, Shuangyi ^a   Aubele, Danielle L ^a   Floreancig, Paul E ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; CARBENOID; EPOXIDE; ETHER DERIVATIVE; OXOCARBENIUM; TETRAHYDROPYRANYL ETHER; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; OXIDATION; PRIORITY JOURNAL;

EID: 27944493948     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.08.055     Document Type: Article

References (41)

1. L.F. Tietze Chem. Rev. 96 1996 115
2. For recent examples, see: W.D. Kerber, and M.R. Gagné Org. Lett. 7 2005 3379
3. C. Nieto-Oberhuber, S. López, and A.M. Echavarren J. Am. Chem. Soc. 127 2005 6178
4. Z. Xiong, and E.J. Corey J. Am. Chem. Soc. 122 2000 4831
5. W.C. Still, and A.G. Romero J. Am. Chem. Soc. 108 1986 2105
6. J.E. Baldwin J. Chem. Soc., Chem. Commun. 1976 738
7. J. Na, K.N. Houk, C.G. Shevlin, K.D. Janda, and R.A. Lerner J. Am. Chem. Soc. 115 1993 8453
8. K.C. Nicolaou, C.V.C. Prasad, P.K. Somers, and C.-K. Hwang J. Am. Chem. Soc. 111 1989 5330
9. T.P. Heffron, and T.F. Jamison Org. Lett. 5 2003 2339
10. J.C. Valentine, F.E. McDonald, W.A. Neiwart, and K.I. Hardcastle J. Am. Chem. Soc. 127 2005 4586
11. F.E. McDonald, F. Bravo, X. Wang, X. Wei, M. Toganoh, R. Rodríguez, B. Do, W.A. Neiwart, and K.I. Hardcastle J. Org. Chem. 67 2002 2515
12. F.E. McDonald, X. Wang, B. Do, and K.I. Hardcastle Org. Lett. 2 2000 2917
13. A. Zakarian, A. Batch, and R.A. Holton J. Am. Chem. Soc. 125 2003 7822
14. E. Alvarez, M.T. Díaz, R. Pérez, J.L. Ravelo, J.A. Vera, D. Zurita, and J.D. Martín J. Org. Chem. 59 1994 2848
15. F. Bravo, F.E. McDonald, W.A. Neiwart, and K.I. Hardcastle Org. Lett. 6 2004 4487
16. For other additions of ethers into halonium ions, see: N. Khan, H. Xiao, B. Zhang, X. Cheng, and D.R. Mootoo Tetrahedron 55 1999 8303
17. D.B. Collum, J.H. McDonald III, and W.C. Still J. Am. Chem. Soc. 102 1980 2120
18. S.H. Tang, and R.M. Kennedy Tetrahedron Lett. 33 1992 5299
19. F.E. McDonald, and T.B. Towne J. Am. Chem. Soc. 116 1994 7921
20. T.J. Donohoe, and S. Butterworth Angew. Chem., Int. Ed. 42 2003 948
21. V. Piccialli, and T. Caserta Tetrahedron Lett. 45 2004 303
22. T.J. Donohoe, and S. Butterworth Angew. Chem., Int. Ed. 44 2005 4766
23. V.S. Kumar, and P.E. Floreancig J. Am. Chem. Soc. 123 2001 3842
24. D.L. Aubele, and P.E. Floreancig Org. Lett. 4 2002 3443
25. For a preliminary account of this work, see: V.S. Kumar, D.L. Aubele, and P.E. Floreancig Org. Lett. 4 2002 3443
26. V.S. Kumar, D.L. Aubele, and P.E. Floreancig Org. Lett. 3 2001 4123
27. For alkoxy group delivery through mixed acetals in carbohydrate synthesis, see: F. Barresi, and O. Hindsgaul J. Am. Chem. Soc. 113 1991 9376
28. Z.-X. Wang, Y. Tu, M. Frohn, J.-R. Zhang, and Y. Shi J. Am. Chem. Soc. 119 1997 11224
29. Y. Tu, Z.-X. Wang, and Y. Shi J. Am. Chem. Soc. 118 1996 9806
30. For a related approach to the enantioselective synthesis of bis-epoxides, see Ref. 7.
31. An exact determination of the relative diastereomeric ratio of the epoxides was not possible due to the presence of other randomized stereocenters in the molecule.
32. Y. Gao, R.M. Hanson, J.M. Klunder, S.Y. Ko, H. Masamune, and K.B. Sharpless J. Am. Chem. Soc. 109 1987 5765
33. T. Katsuki, and K.B. Sharpless J. Am. Chem. Soc. 102 1980 5974
34. P.K. Jadhav, K.S. Bhat, P.T. Perumal, and H.C. Brown J. Org. Chem. 51 1986 432
35. H.C. Brown, and P.K. Jadhav J. Am. Chem. Soc. 105 1983 2092
36. K. Koide, J.M. Finkelstein, Z. Ball, and G.L. Verdine J. Am. Chem. Soc. 123 2001 398
37. V.S. Martin, S.S. Woodard, T. Katsuki, Y. Yamada, M. Ikeda, and K.B. Sharpless J. Am. Chem. Soc. 103 1981 6237
38. L.J. Liotta, K.L. Dombi, S.A. Kelley, S. Targontsidis, and A.M. Morin Tetrahedron Lett. 38 1997 7833
39. J. Stanek, M. Marek, and J. Jary Carbohydr. Res. 64 1978 315
40. G. Grethe, T. Mitt, T.H. Williams, and M. Uskokovic J. Org. Chem. 48 1983 5309
41. The chemical shift of the hydrogen at the anomeric center is highly characteristic of tetrahydrofuranyl ethers (≥5.0 ppm) and tetrahydropyranyl ethers (∼4.6 ppm).