Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 20-21, Pages 3715-3718Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100264
Keywords
Metalation; Chiral auxiliaries; Sandwich complexes; Lithium; Carbohydrates
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Funding
- Rennes Metropole, Institut Universitaire de France, Region Bretagne
- University of Rennes
- Centre National de la Recherche Scientifique (CNRS)
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The ability of a mixed lithium-cadmium amide to deproto-metallate diastereoselectively several sugar-derived ferrocene esters was studied. The ferrocenecarboxylates generated from alpha-D-glucofuranoses gave the best results, as evidenced after subsequent trapping with iodine. Good chemical yields and diastereoselectivities up to 82% in favor of the S-P stereoisomer were obtained. The use of a different chiral group favored the formation of the R-P stereoisomer, isolated in 34% yield and 98% diastereoselectivity.
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