Intramolecular regioselective addition of radicals and carbanions to ynol ethers. A strategy for the synthesis of exocyclic enol ethers

Tetrahedron

Volumn 67, Issue 1, 2011, Pages 92-99

  Hanna, Rana ^a   Daoust, Benoit ^a  

^a UNIVERSITÉ DU QUÉBEC À TROIS RIVIÈRES   (Canada)

Author keywords

Alkyllithiums; Anionic cyclization; Enol ethers; Radical cyclization; Vinyllithiums; Ynol ethers

Indexed keywords

(CARBOETHOXYMENTHOXYMETHYLENE)CYCLOPENTANE; (ETHOXYIODOMETHYLENE)CYCLOHEXANE; (ETHOXYIODOMETHYLENE)CYCLOPENTANE; (MENTHOXYCARBOXALDEHYDEMETHYLENE)CYCLOPENTANE; (MENTHOXYIODOMETHYLENE)CYCLOPENTANE; (MENTHOXYMETHYLENE)CYCLOPENTANE; 1 CYCLOPENTYLIDENE 1 ETHOXY 2,4 DIMETHYLPENTAN 2 OL; 1 MENTHOXYHEPTYNE; 1 MENTHOXYHEXYNE; 2 CYCLOPENTYLIDENE 2 ETHOXY 1 PHENYLETHANOL; 6 IODO 1 ETHOXYHEXYNE; 6 IODO 1 METHOXYHEXYNE; 7 IODO 1 ETHOXYHEXYNE; 7 IODO 1 METHOXYHEXYNE; ALKYL GROUP; ALKYNE DERIVATIVE; ANION; CARBON; ETHER; ETHER DERIVATIVE; EXOCYCLIC DOUBLE BOND; IODINE; LITHIUM DERIVATIVE; OXYGEN; RADICAL; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ELECTROPHILICITY; HYDROLYSIS; PRIORITY JOURNAL; SYNTHESIS;

EID: 78649796968     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.11.024     Document Type: Article

References (21)

1. D.P. Curran, M.-H. Chen, and D. Kim J. Am. Chem. Soc. 111 1989 6265
2. D.P. Curran, and D. Kim Tetrahedron 47 1991 6171
3. W.F. Bailey, and T.V. Ovaska J. Am. Chem. Soc. 115 1993 3080
4. M.P.J. Cooke, and D. Gopal J. Org. Chem. 59 1994 260
5. M.P.J. Cooke J. Org. Chem. 58 1993 6833
6. T. Ohnuki, M. Yoshida, and O. Simamura Chem. Lett. 1972 797
7. R.L. Funk, G.L. Bolton, K.M. Brummond, K.E. Ellestad, and J.B. Stallman J. Am. Chem. Soc. 115 1993 7023
8. G. Gralla, B. Wibbeling, and D. Hoppe Org. Lett. 4 2002 2193
9. F. Longpre, N. Rusu, M. Larouche, R. Hanna, and B. Daoust Can. J. Chem. 86 2008 970
10. P. Lemoine, and B. Daoust Tetrahedron Lett. 49 2008 6175
11. A. Moyano, F. Charbonnier, and A.E. Greene J. Org. Chem. 52 1987 2919
12. M.P.J. Cooke J. Org. Chem. 49 1984 1144
13. M.P.J. Cooke, and R.K. Widener J. Org. Chem. 52 1987 1381
14. W.F. Bailey, A.D. Kbanolkar, K. Gavaskar, T.V. Ovaska, K. Rossi, Y. Thiel, and K.B. Wiberg J. Am. Chem. Soc. 113 1991 5720
15. J.G. Kooyman, H.P.G. Hendriks, P.P. Montijn, L. Brandsma, and J.F. Arens Recl. Trav. Chim. Pays-Bas 87 1968 69
16. G. Mehta, and K.S. Rao J. Am. Chem. Soc. 108 1986 8015
17. Q. Ye, and G.L. Grunewald J. Med. Chem. 32 1989 478
18. H. Rudler, A. Parlier, T. Durand-Réville, B. Martin-Vaca, M. Audouin, E. Garrier, V. Certal, and J. Vaissermann Tetrahedron 56 2000 5001
19. J.C. Gilbert, and U. Weerasooriya J. Org. Chem. 48 1983 448
20. M.S. Newman, and O.M. Okorodudu J. Org. Chem. 34 1969 1220
21. D. Reisdorf, and H. Normant Organomet. Chem. Synth. 1 1972 393