Abstract

By reaction with aromatic Grignard reagents in the presence of low valent nickel species at low temperature, the 1,2-unsaturated furanoid glycal ( 1) undergoes coupling reaction to produce 2,3-unsaturated products ( 1a,b) as pure stereoisomers. When these reaction conditions are applied to protected 1,2-unsaturated pyranoid glycals ( 2, 3, 4), both cross-coupling and elimination reactions occur to give conjugated diene-alcohol derivatives ( 2a; 3a,b; 4a,b, respectively), in moderate yield.

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