Cascade Approach to Stereoselective Poly cyclic Ether Formation: Epoxides as Trapping Agents in the Transposition of Allylic Alcohols

摘要

Cascade reactions facilitate complex molecule synthesis through their capacity to generate multiple target-relevant bonds and stereocenters in a single operation. The use of thermodynamic control to dictate product formation further streamlines molecular synthesis by minimizing the need to set multiple stereocenters in the substrates. Rhenium oxide mediated allylic alcohol transpositions are useful in the design of thermodynamically controlled reactions because regiochemistry and stereochemistry are influenced by structural changes. Thus, they are being used increasingly in complex molecule synthesis. A schematic of the process that is consistent with experimental observations and computational studies is shown in Scheme 1.