An Enantiomerically Pure Epoxyorganolithium Reagent for the Synthesis of Oligo(tetrahydrofurans) by an Epoxide-Cascade Reaction

Article abstract of DOI:10.1016/S0040-4039(00)78360-2

Enantiomerically pure oligo(tetrahydrofurans) 17 and 18 have been prepared using an epoxide cascade reaction.The polyepoxide precursors 13 and 14 were synthesized using the enantiomerically pure epoxyorganolithium reagent 3.Thus, addition of 3 to the THF aldehyde 11 gave alcohol 12 with a high Cram selectivity of 95:5.