Asymmetric Additions to Dichlorophenyldioxane, A New Chiral Acetal

Article abstract of DOI:10.1016/0040-4039(95)01960-P

4-(2,6-Dichlorophenyl)-1,3-dioxanes have been reacted with weak nucleophiles and TiCl4 to give benzyl ethers with high selectivity.The major products are consistent with an S_N2-like mechanism.The benzyl ether is removed in one step using Li/NH3 to give non-racemic secondary alcohols.