Benzyne arylation of oxathiane glycosyl donors

• Martin A. Fascione and
• W. Bruce Turnbull

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 oxathiane glycosyl donors 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; oxathiane glycosyl donors

• of novel oxathiane glycosyl donors 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