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ChemInform Abstract: Double Stereodifferentiation in the Lewis Acid Promoted C- Glycosidation of Activated Glycals with Chiral (E)-Crotylsilanes.

✍ Scribed by J. S. PANEK; J. V. SCHAUS

Publisher: John Wiley and Sons
Year: 2010
Weight: 31 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199752040

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✦ Synopsis

Double Stereodifferentiation in the Lewis Acid Promoted C-Glycosidation of Activated Glycals with Chiral (E)-Crotylsilanes.

-It is shown that the pairwise combination of the glycals (I) and (V) with the chiral silanes (II) affords high levels of selectivity resulting from the existence of strong stereochemical control elements within each reaction component. The topological bias is principally controlled by stereoelectronic effects of the pyran oxonium ion and by the facial bias of the silane (II). Consistent with the behavior of the silanes (II) and an anti-SE' mechanism of the 4 possible diastereomers, only the 2 isomers derived from the C1' stereochemical relationship are detectable. -(PANEK,

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