We have reported an efficient gold(I)-catalyzed tandem cyclization of
tert-butyl carbonate derivatives of hex-1-en-5-
yn-3-ol where nucleophilicparticipation of the
O-Boc group appears to intercept a carbocationic (or cyclopropyl carbene) Au intermediate. This novel protocol leads todensely functionalized cyclohexene-3,4-diol derivatives where 1,2- or 1,2,3-stereocenters are controlled in a highly diastereoselective fa
shion.