Tertiary alcohols by tandem β-carbolithiation and N→C aryl migration in enol carbamates

Organic Letters

Volumn 14, Issue 1, 2012, Pages 142-145

  Fournier, Anne M ^a   Clayden, Jonathan ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CARBAMIC ACID DERIVATIVE; CARBON; NITROGEN; VINYL DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ALCOHOLS; ALKYLATION; CARBAMATES; CARBON; MOLECULAR STRUCTURE; NITROGEN; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 84855480270     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2029355     Document Type: Article

References (30)

1. Clayden, J.; Dufour, J.; Grainger, D.; Helliwell, M. J. Am. Chem. Soc. 2007, 129, 7488
2. Clayden, J.; Hennecke, U. Org. Lett. 2008, 10, 3567
3. Bach, R.; Clayden, J.; Hennecke, U. Synlett 2009, 421
4. Tetlow, D. J.; Hennecke, U.; Raftery, J.; Waring, M. J.; Clarke, D. S.; Clayden, J. Org. Lett. 2010, 12, 5442
5. Clayden, J.; Farnaby, W.; Grainger, D. M.; Hennecke, U.; Mancinelli, M.; Tetlow, D. J.; Hillier, I. H.; Vincent, M. A. J. Am. Chem. Soc. 2009, 131, 3410
6. Fournier, A. M.; Brown, R. A.; Farnaby, W.; Miyatake-Ondozabal, H.; Clayden, J. Org. Lett. 2010, 12, 2222
7. Peters, J. G.; Seppi, M.; Fröhlich, R.; Wibbeling, B.; Hoppe, D. Synthesis 2002, 3, 381
8. Superchi, S.; Sotomayor, N.; Miao, G.; Joseph, B.; Campbell, M. G.; Snieckus, V. Tetrahedron Lett. 1996, 37, 6061
9. Whisler, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem., Int. Ed. 2004, 43, 2206
10. Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 19, 356
11. Rondan, N. G.; Houk, K. N.; Beak, P.; Zajdel, W. J.; Chandrasekhar, J.; Scheleyer, P. R. J. Org. Chem. 1981, 46, 4108
12. Wei, X.; Taylor, R. J. K. Chem. Commun. 1996, 187
13. Wei, P.; Johnson, P.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 2000, 1109
14. Clayden, J.; Donnard, M.; Lefranc, J.; Minassi, A.; Tetlow, D. J. J. Am. Chem. Soc. 2010, 132, 6624
15. Hogan, A.-M. L.; O'Shea, D. F. Chem. Commun. 2008, 3839
16. Jiang, X.-B.; van der Berg, M.; Minnaard, A. J.; Feringa, B. L.; de Vries, J. G. Tetrahedron: Asymmetry 2004, 15, 2223
17. E -Alkenylcarbamates have also been made by stereoselective carbometallation of alkynylcarbamates; see: Chechik-Lankin, H.; Marek, I. Org. Lett. 2005, 5, 5087
18. Bates, R. B.; Kroposki, L. M.; Potter, D. E. J. Org. Chem. 1972, 37, 560
19. Jung, M. E.; Blum, R. B. Tetrahedron Lett. 1977, 43, 3791
20. Clayden, J.; Yasin, S. A. New J. Chem. 2002, 26, 191
21. Sengupta, S.; Snieckus, V. J. Org. Chem. 1990, 55, 5680
22. Snieckus, V. Pure Appl. Chem. 1990, 62, 2047
23. Chedid, R. B.; Brummer, M.; Wibbeling, B.; Fröhlich, R.; Hoppe, D. Angew. Chem., Int. Ed. 2007, 46, 3131
24. Klein, S.; Marek, I.; Poisson, J. F.; Normant, J. F. J. Am. Chem. Soc. 1995, 117, 8853
25. Norsikian, S.; Marek, I.; Klein, S.; Poisson, J. F.; Normant, J. F. Chem.-Eur. J. 1999, 5, 2055
26. Hogan, A.-M. L.; O'Shea, D. F. J. Org. Chem. 2008, 73, 2503
27. Basu, A.; Thayumanavan, S. Angew. Chem., Int. Ed. 2002, 41, 716
28. Dreller, S.; Dyrbusch, M.; Hoppe, D. Synlett 1991, 397
29. Schultz-Fademrecht, C.; Wibbeling, B.; Fröhlich, R.; Hoppe, D. Org. Lett. 2001, 3, 1221
30. Tomida, Y.; Nagaki, A.; Yoshida, J.-I. J. Am. Chem. Soc. 2011, 133, 3744