Beilstein J. Org. Chem.2010,6, No. 19, doi:10.3762/bjoc.6.19
Martin A. Fascione W. Bruce Turnbull School of Chemistry, University of Leeds, Leeds, LS2 9JT, UK 10.3762/bjoc.6.19 Abstract The arylation of bicyclic oxathianeglycosyldonors has been achieved using benzyne generated in situ from 1-aminobenzotriazole (1-ABT) and lead tetraacetate. Following
sulfur arylation, glycosylation of acetate ions proceeded with high levels of stereoselectivity to afford α-glycosyl acetates in a ‘one-pot’ reaction, even in the presence of alternative acceptor alcohols.
Keywords: benzyne; 1,2-cis-glycosides; glycosyl acetates; oxathianeglycosyldonors
of novel oxathianeglycosyldonors can be achieved using a combination of 1-ABT and lead tetraacetate. Following arylation, glycosylation with an acetate anion takes place with a high degree of stereoselectivity to afford 1,2-cis-α-acetates.
a) Boons’ chiral auxiliary-based approach to α
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Graphical Abstract
Scheme 1:
a) Boons’ chiral auxiliary-based approach to α-stereoselective glycosylations. b) Modified strategy...