Novel lactonization with phenonium ion participation induced by hypervalent iodine reagents

Organic Letters

Volumn 5, Issue 12, 2003, Pages 2157-2159

  Boye, Amanda C ^a   Meyer, Dominik ^b   Ingison, Crystal K ^a   French, Andrew N ^a   Wirth, Thomas ^c  

^a ALBION COLLEGE   (United States)

^b UNIVERSITY OF BASEL   (Switzerland)

^c CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; IODINE; ION; LACTONE DERIVATIVE; PHENONIUM ION; UNCLASSIFIED DRUG; VALERIC ACID DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS;

EID: 0141854098     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034616f     Document Type: Article

References (33)

1. (a) Cram, D. J. J. Am. Chem. Soc. 1949, 71, 3863.
2. (b) Cram, D. J.; Davis, R. J. Am. Chem. Soc. 1949, 71, 3871.
3. (c) Cram, D. J. J. Am. Chem. Soc. 1949, 71, 3875.
4. (d) Cram, D. J. J. Am. Chem. Soc. 1964, 86, 3767.
5. (e) Brown, H. C.; Morgan, K. J.; Chloupek, F. J. J. Am. Chem. Soc. 1965, 87, 2137.
6. (a) Vogel, P. In Carbocation Chemistry; Elsevier: Amsterdam, 1985; Chapter 7.
7. (b) Olah, G. A.; Porter, R. D. J. Am. Chem. Soc. 1970, 92, 7627.
8. (c) Del Rio, E.; Menéndez, M. I.; López, R.; Sordo, T. L. J. Phys. Chem. A 2000, 104, 5568.
9. (a) Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: Oxford, 1997.
10. (b) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271.
11. (c) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
12. (d) Wirth, T., Ed. Top. Curr. Chem. 2003, 224.
13. Shah, M.; Taschner, M. J.; Koser, G. F.; Rach, N. L. Tetrahedron Lett. 1986, 27, 4557.
14. (a) Stang, P. J.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 85.
15. (b) Ochiai, M. In Chemistry of Hypervalent Compounds; Wiley-VCH: Akiba, K., Ed.; New York, 1999, 359.
16. Rebrovic, L.; Koser, G. F. J. Org. Chem. 1984, 49, 2462.
17. Prakash, O.; Pahuja, S.; Goyal, S.; Sawhney, S. N.; Moriarty, R. M. Synlett 1990, 337.
18. +) calcd, 252.1236; found, 252.1234.
19. Betancourt de Perez, R. M.; Fuentes, L. M.; Larson, G. L.; Barnes, C. L. ; Heeg, M. J. J. Org. Chem. 1986, 51, 2039.
20. Wirth, T. Angew. Chem., Int. Ed. 2001, 40, 2812.
21. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
22. (b) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
23. Gilchrist, T. L.; Kemmitt, P. D.; Germain, A. L. Tetrahedron 1997, 53, 4447.
24. +) calcd, 266.1392; found, 266.1389.
25. (a) Nagumo, S.; Furukawa, T.; Ono, M.; Akita, H. Tetrahedron Lett. 1997, 38, 2849.
26. (b) Nagumo, S.; Hisano, T.; Kakimoto, Y.; Kawahara, N.; Ono, M.; Furukawa, T.; Takeda, S.; Akita, H. Tetrahedron Lett. 1998, 40, 8109.
27. (c) Nagumo, S.; Ishii, Y.; Kakimoto, Y.; Kawahara, N. Tetrahedron Lett. 2002, 43, 5333.
28. (d) Nagumo, S.; Ono, M.; Kakimoto, Y.; Furukawa, T.; Hisano, T.; Mizukami, M.; Kawahara, N.; Akita, H. J. Org. Chem. 2002, 67, 6618.
29. -1.
30. Hirt, U. H.; Schuster, M. F. H.; French, A. N.; Wiest, O. G.; Wirth, T. Eur. J. Org. Chem. 2001, 1569.
31. Separation of the enantiomers: Daicel OD-H, hexane/2-propanol 9:1, t(minor) = 33.0 min, t(major) = 38.4 min.
32. Haas, J.; Piguel, S.; Wirth, T. Org. Lett. 2002, 4, 297.
33. McKillop, A.; Kemp, D. Tetrahedron 1989, 45, 3299.