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Volumn , Issue 5, 2005, Pages 781-784

C1-symmetric aminosulfoximines as ligands in copper-catalyzed carbonyl-ene reactions

Author keywords

hydroxy esters; Asymmetric catalysis; Carbonyl ene reactions; Copper; Sulfoximines

Indexed keywords

ALKENE; AMINOSULFOXIMINE DERIVATIVE; CARBONYL DERIVATIVE; COPPER; ESTER; IMINE; LIGAND; PYRUVIC ACID DERIVATIVE; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

EID: 15944401744     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-863737     Document Type: Article
Times cited : (33)

References (50)
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    • For Cu-catalyzed cycloaddition reactions, see: (a) Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830.
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    • Bolm, C.1    Simic, O.2
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    • 0035208607 scopus 로고    scopus 로고
    • For Pd-catalyzed allylic alkylations, see: (a) Bolm, C.; Simic, O.; Martin, M. Synlett 2001, 12, 1878.
    • (2001) Synlett , vol.12 , pp. 1878
    • Bolm, C.1    Simic, O.2    Martin, M.3
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    • Langner, M.; Bolm, C. Angew. Chem. Int. Ed. 2004, 43, 5984; Angew. Chem. 2004, 116, 6110.
    • (2004) Angew. Chem. , vol.116 , pp. 6110
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    • (e) Yuan, Y.; Zhang, X.; Ding, K. Angew. Chem. Int. Ed. 2003, 42, 5478; Angew. Chem. 2003, 115, 5636.
    • (2003) Angew. Chem. , vol.115 , pp. 5636
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    • Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin
    • (h) See also: Mikami, K.; Terada, M. In Comprehensive Asymmetric Catalysis, Vol. III; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, 1143.
    • (1999) Comprehensive Asymmetric Catalysis , vol.3 , pp. 1143
    • Mikami, K.1    Terada, M.2
  • 48
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    • note
    • A pronounced effect of ortho-alkoxy groups was observed in hetero-Diels-Alder reactions catalyzed by copper complexes bearing N-quinolyl sulfoximines. For details, see ref. 11.
  • 49
    • 15944370822 scopus 로고    scopus 로고
    • note
    • 2O (50 mL) and filtered through a plug of silica gel. The solvent was removed under reduced pressure, and the corresponding product was purified by column chromatography (pentane-EtOAc, 15:1 for 9a and 9c, 10:1 for 9b) and obtained as colorless oil.
  • 50
    • 15944365024 scopus 로고    scopus 로고
    • note
    • Unfortunately, 9b was obtained as a mixture with enophile 7b, which was inseparable by column chromatography. Use of (chiral) HPLC, however, allowed the determination of the enantiomeric ratio of 9b (80% ee). The 'yield' of 9b was then estimated from the NMR spectra (44%).


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