S_N2 Reactions at Tertiary Carbon Centers in Epoxides

Described herein is a novel concept for S_N 2 reactions at tertiary carbon centers in epoxides without activation of the leaving group. Quantum chemical calculations show why S_N 2 reactions at tertiary carbon centers are proceeding in these systems. The reaction allows flexible synthesis of 1,3-diol building blocks for natural product synthesis with excellent control of the relative and absolute configurations.