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Synlett 1998; 1998(4): 425-427
DOI: 10.1055/s-1998-3130
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Addition of Tri-O-benzyl-2-deoxy-d-glucosylcopper(I) to Cationic CpMo(NO)(CO)(5-methyl-2,3,4-η-hex-3-en-2-yl) Complexes. A New Approach to C-Glycosides

John A. Christopher* , Philip J. Kocienski, Martin J. Procter
  • *Department of Chemistry, Glasgow University, Glasgow G12 8QQ, UK
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Publication Date:
31 December 2000 (online)

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The reaction of tri-O-benzyl-2-deoxyglucosylcopper(I) reagents with (η5-cyclopentadienyl)(5-methyl-2,3,4-η-hex-3-en-2-yl)(carbonyl)(nitrosyl)molybdenum tetrafluoroborate complexes derived from homochiral allylic acetates occurs with high regiocontrol and enantiofacial control to give C-glycosides. An electronic effect attributed to the nitrosyl ligand which normally governs the regiochemistry of the alkylation has been subverted.

asymmetric alkylation - C-glycoside - molybdenum - glycosylcopper(I) - π-allyl complex

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