Metalated nitriles: Electrophile-dependent alkylations

Organic Letters

Volumn 7, Issue 3, 2005, Pages 447-449

  Fleming, Fraser F ^a   Zhang, Zhiyu ^a   Wei, Guoqing ^a   Steward, Omar W ^a  

^a DUQUESNE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CARBONYL DERIVATIVE; CYANIDE; HALIDE; KETONE; NITRILE; SULFONIC ACID DERIVATIVE;

ACYLATION; ALKYLATION; ARTICLE; CONJUGATE; DIASTEREOISOMER; STEREOCHEMISTRY;

ALDEHYDES; ALKYLATION; CYANIDES; KETONES; METALS; MOLECULAR CONFORMATION; NITRILES; STEREOISOMERISM;

EID: 13844297054     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047598q     Document Type: Article

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23. Although unusual, C-metalated nitriles are known for Li, Mg, and Zn: (a) Boche, G.; Harms, K.; Marsch, M. J. Am. Chem. Soc. 1988, 110, 6925. (b) Thibonnet, J.; Vu, V. A.; Berillon, L.; Knochel, P. Tetrahedron 2002, 58, 4787. (c) Goasdoue, N.; Gaudemar, M. J. Organomet. Chem. 1972, 39, 17. For alkylations of chiral Grignard reagents, see: Hoffmann, R. W. Chem. Soc. Rev. 2003, 32, 225.
24. Although unusual, C-metalated nitriles are known for Li, Mg, and Zn: (a) Boche, G.; Harms, K.; Marsch, M. J. Am. Chem. Soc. 1988, 110, 6925. (b) Thibonnet, J.; Vu, V. A.; Berillon, L.; Knochel, P. Tetrahedron 2002, 58, 4787. (c) Goasdoue, N.; Gaudemar, M. J. Organomet. Chem. 1972, 39, 17. For alkylations of chiral Grignard reagents, see: Hoffmann, R. W. Chem. Soc. Rev. 2003, 32, 225.
25. Although unusual, C-metalated nitriles are known for Li, Mg, and Zn: (a) Boche, G.; Harms, K.; Marsch, M. J. Am. Chem. Soc. 1988, 110, 6925. (b) Thibonnet, J.; Vu, V. A.; Berillon, L.; Knochel, P. Tetrahedron 2002, 58, 4787. (c) Goasdoue, N.; Gaudemar, M. J. Organomet. Chem. 1972, 39, 17. For alkylations of chiral Grignard reagents, see: Hoffmann, R. W. Chem. Soc. Rev. 2003, 32, 225.
26. Stereochemical assignments are based on X-ray analysis for 6a-e,g,h, with the crystallographic data being deposited with the Cambridge Crystallographic Data Center (CCDC 218678, 242090, 242091, 242092, 242093, 24209, and 242095, respectively). The supplementary crystallographic data can be obtained free of charge via the Internet at www.c-cdc.cam.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge CB2 1EZ, UK (fax +44 1223 336033; or e-mail deposit@ccdc.cam.ac.uk).
27. 4), concentrated, and purified by radial chromatography to afford the pure nitrile.
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