Catalysis of the Michael addition reaction by late transition metal complexes of BINOL-derived salens

Journal of Organic Chemistry

Volumn 68, Issue 5, 2003, Pages 1973-1981

  Annamalai, Venkatachalam ^a   DiMauro, Erin F ^a   Carroll, Patrick J ^a   Kozlowski, Marisa C ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROPHILES;

CATALYSIS; CATALYSTS; INORGANIC ACIDS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

TRANSITION METALS;

2 CYCLOHEXENONE; 2,2' DIHYDROXY 1,1' BINAPHTHYL; ALCOHOL DERIVATIVE; CESIUM; LEWIS ACID; MALONIC ACID DERIVATIVE; METAL COMPLEX; NICKEL; SALEN; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; CRYSTAL STRUCTURE; MICHAEL ADDITION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CATALYSIS; CESIUM; CRYSTALLOGRAPHY, X-RAY; INDICATORS AND REAGENTS; KINETICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NAPHTHOLS; NICKEL; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 0037424485     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo025993t     Document Type: Article

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36. Reaction time was 48 h at 20, 0, and -20 °C and 5 d at -40 °C.
37. For example: Mockler, G. M.; Chaffey, G. W.; Sinn, E.; Wong, H. Inorg. Chem. 1972, 11, 1308-1314.
38. Examination of nickel salen complexes in the Cambridge Structural Database (The United Kingdom Chemical Database Service: Fletcher, D. A.; McMeeking, R. F.; Parkin, D. J. Chem. Inf. Comput. Sci. 1996, 36, 746) revealed square-pyramidal or octahedral adducts upon coordination of further ligands. In general, the salen ligand coordinates in a square-planar array. Square pyramidal: (a) Elerman, Y.; Kabak, M.; Atakol, O. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1993, 49, 1905-1906. (b) Clarke, N.; Cunningham, D.; Higgins, T.; McArdle, P.; McGinley, J.; O'Gara, M. J. Organomet. Chem. 1994, 469, 33-40. Octahedral: (c) Gomes, L.; Sousa, C.; Freire, C.; de Castro, B. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2000, 56, 1201-1203.
39. Examination of nickel salen complexes in the Cambridge Structural Database (The United Kingdom Chemical Database Service: Fletcher, D. A.; McMeeking, R. F.; Parkin, D. J. Chem. Inf. Comput. Sci. 1996, 36, 746) revealed square-pyramidal or octahedral adducts upon coordination of further ligands. In general, the salen ligand coordinates in a square-planar array. Square pyramidal: (a) Elerman, Y.; Kabak, M.; Atakol, O. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1993, 49, 1905-1906. (b) Clarke, N.; Cunningham, D.; Higgins, T.; McArdle, P.; McGinley, J.; O'Gara, M. J. Organomet. Chem. 1994, 469, 33-40. Octahedral: (c) Gomes, L.; Sousa, C.; Freire, C.; de Castro, B. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2000, 56, 1201-1203.
40. Examination of nickel salen complexes in the Cambridge Structural Database (The United Kingdom Chemical Database Service: Fletcher, D. A.; McMeeking, R. F.; Parkin, D. J. Chem. Inf. Comput. Sci. 1996, 36, 746) revealed square-pyramidal or octahedral adducts upon coordination of further ligands. In general, the salen ligand coordinates in a square-planar array. Square pyramidal: (a) Elerman, Y.; Kabak, M.; Atakol, O. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1993, 49, 1905-1906. (b) Clarke, N.; Cunningham, D.; Higgins, T.; McArdle, P.; McGinley, J.; O'Gara, M. J. Organomet. Chem. 1994, 469, 33-40. Octahedral: (c) Gomes, L.; Sousa, C.; Freire, C.; de Castro, B. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2000, 56, 1201-1203.
41. Examination of nickel salen complexes in the Cambridge Structural Database (The United Kingdom Chemical Database Service: Fletcher, D. A.; McMeeking, R. F.; Parkin, D. J. Chem. Inf. Comput. Sci. 1996, 36, 746) revealed square-pyramidal or octahedral adducts upon coordination of further ligands. In general, the salen ligand coordinates in a square-planar array. Square pyramidal: (a) Elerman, Y.; Kabak, M.; Atakol, O. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1993, 49, 1905-1906. (b) Clarke, N.; Cunningham, D.; Higgins, T.; McArdle, P.; McGinley, J.; O'Gara, M. J. Organomet. Chem. 1994, 469, 33-40. Octahedral: (c) Gomes, L.; Sousa, C.; Freire, C.; de Castro, B. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2000, 56, 1201-1203.
42. For reviews on nonlinear effects, see: (a) Blackmond, D. G. J. Am. Chem. Soc. 1997, 119, 12934-12939. (b) Guillaneux, D.; Zhao, S.; Samuel, O.; Rainford, D.; Kagan, H. B. J. Am. Chem. Soc. 1994, 116, 9430-9439. (c) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. 1998, 37, 2922-2959.
43. For reviews on nonlinear effects, see: (a) Blackmond, D. G. J. Am. Chem. Soc. 1997, 119, 12934-12939. (b) Guillaneux, D.; Zhao, S.; Samuel, O.; Rainford, D.; Kagan, H. B. J. Am. Chem. Soc. 1994, 116, 9430-9439. (c) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. 1998, 37, 2922-2959.
44. For reviews on nonlinear effects, see: (a) Blackmond, D. G. J. Am. Chem. Soc. 1997, 119, 12934-12939. (b) Guillaneux, D.; Zhao, S.; Samuel, O.; Rainford, D.; Kagan, H. B. J. Am. Chem. Soc. 1994, 116, 9430-9439. (c) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. 1998, 37, 2922-2959.
45. Present from preparation of the catalyst.
46. 3 (>25d) would be present in the catalyst mix.
47. Since the nondeprotonated adduct (22) is not a catalyst, it seems reasonable that only the half of 35 containing the naphthoate portion can act as a catalyst.