Complete regioselective addition of grignard reagents to pyrazine N-oxides, toward an efficient enantioselective synthesis of substituted piperazines

Organic Letters

Volumn 12, Issue 2, 2010, Pages 284-286

  Andersson, Hans ^a   Banchelin, Thomas Sainte Luce ^a   Das, Sajal ^a   Gustafsson, Magnus ^b   Olsson, Roger ^b,c   Almqvist, Fredrik ^a  

^a UMEÅ UNIVERSITY   (Sweden)

^b ACADIA Pharmaceuticals AB   (Sweden)

^c UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ORGANOMETALLIC COMPOUND; OXIDE; PIPERAZINE DERIVATIVE; PYRAZINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIDES; PIPERAZINES; PYRAZINES; STEREOISOMERISM;

EID: 74949116077     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902619h     Document Type: Article

References (18)

1. (a) Andersson, H.; Almqvist. F.; Olsson, R. Org. Lett. 2007, 9, 1335-1337.
2. (b) Comins, D. L.; Abdullah, A. H. J. Org. Chem. 1982, 47, 4315-4319.
3. (c) Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829-11830.
4. (a) Andersson, H.; Gustafsson, M.; Bostroem, D.; Olsson, R.; Almqvist, F. Angew. Chem., Int. Ed. 2009, 48, 3288-3291.
5. (b) Legault, C.; Charette, A. B. J. Am. Chem. Soc. 2003,125, 6360-6361.
6. (d) Comins, D. L.; Joseph, S. P.; Goehring, R. R. J. Am. Chem. Soc. 1994, 116, 4719-4728.
7. (e) Wang, X.; Kauppi, A. M.; Olsson, R.; Almqvist, F. Eur. J. Org. Chem. 2003, 458, 6-4592.
8. (a) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893-930.
9. (b) Evans, B. E.; Rittle, K. E.; Bock, M. G.; Di Pardo, R. M.; Freidinger, R. M.; Whitter, W. L.; Lundell, G. F.; Veber, D. F.; Anderson, P. S.; Chang, R. S. L.; Lotti, D. J.; Cerino, D. J.; Chen, T. B.; Kling, P. J.; Kunkel, K. A.; Springer, J. P.; Hirshfield, J. J. Med. Chem. 1988, 31, 2235-2246.
10. Vieth, M.; Siegel, M. G.; Higgs, R. E.; Watson, I. A.; Robertson, D. H.; Savin, K. A.; Durst, G. L.; Hipskind, P. A. J. Med. Chem. 2004, 47, 224-232.
11. Ledere, J.-P.; Fagnou, K. Angew. Chem., Int. Ed. 2006, 45, 7781-7786.
12. (a) Nordstrom, L. U.; Madsen, R. Chem. Commun. 2007, 5034-5036.
13. (b) Raw, S. A.; Wilfred, C. D.; Taylor, R. J. K. Chem.Commun. 2003, 2286-2287.
14. Zhou, Y.-G. Acc. Chem. Res. 2007, 40, 1357-1366.
15. (a) Guercio, G.; Bacchi, S.; Goodyear, M.; Carangio, A.; Tinazzi, F.; Curti, S. Org. Process Res. Dev. 2008,12, 1188-1194.
16. (b) Guercio, G.; Manzo, A. M.; Goodyear, M.; Bacchi, S.; Curti, S.; Provera, S. Org. Process Res. Dev. 2009, 13, 489-493.
17. Andersson, H.; Gustafsson, M.; Olsson, R.; Almqvist, F. Tetrahedron Lett. 2008, 49, 6901-6903.
18. Shintani, R.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 1057-1059.