An Au-Catalyzed Cyclialkylation of Electron-Rich Arenes with Epoxides to Prepare 3-Chromanols

Journal of the American Chemical Society

Volumn 126, Issue 19, 2004, Pages 5964-5965

  Shi, Zhangjie ^a   He, Chuan ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; GOLD;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CYCLIZATION; MOLECULAR MECHANICS; STEREOCHEMISTRY; STEREOSPECIFICITY; TEMPERATURE DEPENDENCE;

ANISOLES; BENZENE DERIVATIVES; BENZOPYRANS; CATALYSIS; CYCLIZATION; ELECTRONS; EPOXY COMPOUNDS; GOLD; INDICATORS AND REAGENTS; STEREOISOMERISM;

EID: 2442494249     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja031953a     Document Type: Article

References (27)

1. (a) Xie, D.-Y.; Sharma, S. B.; Paiva, N. L.; Ferreira, D.; Dixon, R. A. Science 2003, 299, 396-399.
2. (b) Krenn, L.; Presser, A.; Pradhan, R.; Bahr, B.; Paper, D. H.; Mayer, K. K.; Kopp, B. J. Nat. Prod. 2003, 66, 1107-1109.
3. (c) Basak, A.; Mandal, S.; Bandyopadhyay, S. Bioorg. Med. Chem. Lett. 2003, 13, 1083-1085.
4. (d) Pan, W.-B.; Chang, F.-R.; Wei, L.-M.; Wu, Y.-C. J. Nat. Prod. 2003, 66, 161-168.
5. (a) Kharasch, M. S.; Isbell, H. S. J. Am. Chem. Soc. 1931, 53, 3053-3059.
6. (b) Liddle, K. S.; Parkin, C. J. Chem. Soc., Chem. Commun. 1972, 26-28.
7. (c) de Graaf, P. W. J.; Boersma, J.; van der Kerk, G. J. M. J. Organomet. Chem. 1976, 105, 399-406.
8. (d) Fuchita, Y.; Utsunomiya, Y.; Yasutake, M. J. Chem. Soc., Dalton Trans. 2001, 2330-2334.
9. (a) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285-2288.
10. (b) Dyker, G.; Muth, E.; Hashmi, A. S. K.; Li, D. Adv. Synth. Catal. 2003, 345. 1247-1252.
11. (a) Reetz, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485-3496.
12. (b) Shi, Z.; He, C. J. Org. Chem., in press.
13. Miyano, S.; Lu, L. D. L.; Viti, S. M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 4350-4360.
14. (a) Rieke, R. D.; Stack, D. E.; Dawson, B. T.; Wu, T.-C. J. Org. Chem. 1993, 58, 2483-2491.
15. (b) Bradsher, C. K.; Reams, D. C. J. Org. Chem. 1978, 43, 3800-3802.
16. (c) Shankaran, K.; Snieckus, V. J. Org. Chem. 1984, 49, 5022-5023.
17. (a) Taylor, S. K.; Hockerman, G. H.; Karrick, G. L.; Lyle, S. B.; Schramm, S. B. J. Org. Chem. 1983, 48, 2450-2452.
18. (b) Taylor, S. K.; Davisson, M. E.; Hissom, B. R., Jr.; Brown, S. L.; Pristach, H. A.; Schramm, S. B.; Harvey, S. M. J. Org. Chem. 1987, 52, 425-429.
19. (a) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974-5976.
20. (b) Yoon, T. P.; Jacobsen, E. N. Science 2003, 299, 1691-1693.
21. (a) Nakajima, T.; Suga, S.; Sugita, T.; Ichikawa, K. Tetrahedron 1969, 25, 1807-1816.
22. (b) Smith, R. A.; Natelson, S. J. Am. Chem. Soc. 1931, 53, 3476-3479.
23. (c) Guest, A.; Hoffman, P. H.; Nugent, M. J. J. Am. Chem. Soc. 1972, 94, 4241-4244.
24. (d) Inoue, M.; Chano, K.; Itoh, O.; Sugita, T.; Ichikawa, K. Bull. Chem. Soc. Jpn. 1980, 53, 458-463.
25. (e) Fráter, G.; Müller, U.; Kraft, P. Helv. Chim. Acta 1999, 82, 1656-1664.
26. (f) Park, B.-D.; Lee, H.-I.; Ryoo, S.-J.; Lee, Y.-S. Tetrahedron Lett. 1997, 38, 591-594.
27. (g) Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 556-556.