Construction of vicinal 4°/3°-carbons via reductive Cope rearrangement

Herein reported is a strategy for constructing vicinal 4 degrees/3 degrees carbons via reductive Cope rearrangement. Substrates have been designed which exhibit Cope rearrangement kinetic barriers of similar to 23 kcal mol(-1) with isoenergetic favorability (Delta G similar to 0). These fluxional/shape-shifting molecules can be driven forward by chemoselective reduction to useful polyfunctionalized building blocks.

Automated summary

A strategy for constructing vicinal 4 degrees/3 degrees carbons via reductive Cope rearrangement is reported herein. Substrates with Cope rearrangement kinetic barriers of approximately 23 kcal mol(-1) and isoenergetic favorability (Delta G approximately 0) have been designed. These fluxional/shape-shifting molecules can be driven forward by chemoselective reduction into useful polyfunctionalized building blocks.