Copper-mediated cross-coupling reactions of N-unsubstituted sulfoximines and aryl halides

Organic Letters

Volumn 6, Issue 19, 2004, Pages 3293-3296

  Gae, Young Cho ^a   Rémy, Pauline ^a   Jansson, Jenny ^a   Moessner, Christian ^a   Bolm, Carsten ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; HALIDE; OXIME DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL REACTION; CROSS COUPLING REACTION; REACTION ANALYSIS;

EID: 4644297662     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048806h     Document Type: Article

References (39)

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32. In this study, racemic 1a was mostly used. For the preparation of enantiomerically pure 1a, see: (a) Fusco, R.; Tericoni, F. Chim. Ind. (Milan) 1965, 47, 61. (b) Johnson, C. R.; Schroeck, C. W. J. Am. Chem. Soc. 1973, 95, 7418. (c) Brandt, J.; Gais, H.-J. Tetrahedron: Asymmetry 1997, 8, 909.
33. In this study, racemic 1a was mostly used. For the preparation of enantiomerically pure 1a, see: (a) Fusco, R.; Tericoni, F. Chim. Ind. (Milan) 1965, 47, 61. (b) Johnson, C. R.; Schroeck, C. W. J. Am. Chem. Soc. 1973, 95, 7418. (c) Brandt, J.; Gais, H.-J. Tetrahedron: Asymmetry 1997, 8, 909.
34. In this study, racemic 1a was mostly used. For the preparation of enantiomerically pure 1a, see: (a) Fusco, R.; Tericoni, F. Chim. Ind. (Milan) 1965, 47, 61. (b) Johnson, C. R.; Schroeck, C. W. J. Am. Chem. Soc. 1973, 95, 7418. (c) Brandt, J.; Gais, H.-J. Tetrahedron: Asymmetry 1997, 8, 909.
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36. 3 and 1.2 equiv of phenyl iodide the yield of 2 was only 24%.
37. R = 44 min (R).
38. For the preparation and synthetic application of 1c, see: Cho, G.-Y.; Okamura, H.; Bolm, C. Manuscript in preparation.
39. As indicated in Scheme 2, the coupling was performed with enantiopure sulfoximine 1a. Only a single diastereomer of 6 was obtained (after column chromatography).