Suppressing the anionic fries rearrangement of aryl dialkylcarbamates; the isolation of a crystalline ortho-deprotonated carbamate

European Journal of Organic Chemistry

Volumn , Issue 4, 2008, Pages 644-647

  García, Felipe ^a   McPartlin, Mary ^a   Morey, James V ^a   Nobuto, Daisuke ^b   Kondo, Yoshinori ^c   Naka, Hiroshi ^c   Uchiyama, Masanobu ^d,e   Wheatley, Andrew E H ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b UNIVERSITY OF TOKYO   (Japan)

^c TOHOKU UNIVERSITY   (Japan)

^d RIKEN   (Japan)

^e TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

Author keywords

Carbamates; Directed ortho metalation; Lithium; Zincates

Indexed keywords

EID: 38949194950     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200701096     Document Type: Article

References (27)

1. For reviews on DoM, see: a) V. Snieckus, Chem. Rev. 1990, 90, 879-933;
2. b) P. Beak, A. I. Meyers, Acc. Chem. Res. 1986, 19, 356-363;
3. c) H. W. Gschwend, H. R. Rodriguez, Org. React. 1979, 26, 1-360;
4. d) J. Clayden, Organolithiums: Selectivity for Synthesis, Pergamon, Oxford, 2002.
5. a) Y. Kondo, M. Shilai, M. Uchiyama, T. Sakamoto, J. Am. Chem. Soc. 1999, 121, 3539-3540;
6. b) M. Uchiyama, T. Miyoshi, Y. Kajihara, T. Sakamoto, Y. Otani, T. Ohwada, Y. Kondo, J. Am. Chem. Soc. 2002, 124, 8514-8515;
7. c) R. E. Mulvey, F. Mongin, M. Uchiyama, Y. Kondo, Angew. Chem. Int. Ed. 2007, 46, 3802-3824 and refs. cited therein;
8. d) M. Uchiyama, Y. Kobayashi, T. Furuyama, S. Nakamura, Y. Kajihara, T. Miyoshi, T. Sakamoto, Y. Kondo, K. Morokuma, J. Am. Chem. Soc., in press.
9. P. C. Andrikopoulos, D. R. Armstrong, H. R. L. Barley, W. Clegg, S. H. Dale, E. Hevia, G. W. Honeyman, A. R. Kennedy, R. E. Mulvey, J. Am. Chem. Soc. 2005, 127, 6184-6185.
10. a) M. Uchiyama, Y. Matsumoto, D. Nobuto, T. Furuyama, K. Yamaguchi, K. Morokuma, J. Am. Chem. Soc. 2006, 128, 8748-8750;
11. b) M. Uchiyama, Y. Matsumoto, S. Usui, Y. Hashimoto, K. Morokuma, Angew. Chem. Int. Ed. 2007, 46, 926-929;
12. c) Y. Kondo, J. V. Morey, J. C. Morgan, H. Naka, D. Nobuto, P. R. Raithby, M. Uchiyama, A. E. H. Wheatley, J. Am. Chem. Soc. 2007, 129, 12734-12738.
13. W. Clegg, S. H. Dale, R. W. Harrington, E. Hevia, G. W. Honeyman, R. E. Mulvey, Angew. Chem. Int. Ed. 2006, 45, 2374-2377.
14. Y. Kondo, N. Takazawa, A. Yoshida, T. Sakamoto, J. Chem. Soc. Perkin Trans. 1 1995, 1207-1208.
15. M. Uchiyama, T. Furuyama, M. Kobayashi, Y. Matsumoto, K. Tanaka, J. Am. Chem. Soc. 2006, 128, 8404-8405.
16. a) J. Clayden, R. P. Davies, M. A. Hendy, R. Snaith, A. E. H. Wheatley, Angew. Chem. Int. Ed. 2001, 40, 1238-1240;
17. b) D. R. Armstrong, J. Clayden, R. Haigh, D. J. Linton, P. Schooler, A. E. H. Wheatley, Chem. Commun. 2003, 1694-1695;
18. c) D. R. Armstrong, S. R. Boss, J. Clayden, R. Haigh, B. A. Kirmani, D. J. Linton, P. Schooler, A. E. H. Wheatley, Angew. Chem. Int. Ed. 2004, 43, 2135-2138;
19. d) K. L. Jantzi, I. A. Guzei, H. J. Reich, Organometallics 2006, 25, 5390-5395.
20. K. J. Singh, D. B. Collum, J. Am. Chem. Soc. 2006, 128, 13753-13760.
21. M. P. Sibi, V. Snieckus, J. Org. Chem. 1983, 48, 1935-1937.
22. a) M. P. Sibi, S. Chattopadhyay, J. W. Dankwardt, V. Snieckus, J. Am. Chem. Soc. 1985, 107, 6312-6315;
23. b) S. L. MacNeil, B. J. Wilson, V. Snieckus, Org. Lett. 2006, 8, 1133-1136.
24. See Supporting Information.
25. G. Bocelli, M. Catellani, G. P. Chiusoli, F. Cugini, B. Lasagni, M. N. Mari, Inorg. Chim. Acta 1998, 270, 123-129.
26. [4]
27. W. Clegg, S. H. Dale, E. Hevia, L. M. Hogg, G. W. Honeyman, R. E. Mulvey, C. T. O'Hara, L. Russo, Angew. Chem. Int. Ed.; DOI: 10.1002/anie. 200704341.