Ketone Chain-Walking Isomerization by Organocatalysis

Key words

isomerization - organocatalysis - chain-walking - sulfur - ketone - reversible transition

Significance

The Morandi group developed a novel and simple method for isomerizing cyclic ketones. To perform this reversible transition, widely available and affordable pyrrolidine and elemental sulfur are used as catalysts. The isomerization of several steroids was demonstrated to access new steroids by using this remarkable ketone chain-walking technique.

Comment

Modifying the placement of functional groups is arguably difficult since it necessitates reversible cleavage and the transposition of strong bonds. Inspired by the Willgerodt–Kindler reaction, the authors succeeded in brilliantly designing a method for the ketone chain-walking isomerization of cyclic ketones enabled by an organocatalyst in combination with elemental sulfur. This low-cost, ecologically friendly approach has the potential to be widely used in the future.

Publication History

Article published online:
14 October 2023