α-Ketol and α-iminol rearrangements in synthetic organic and biosynthetic reactions

In the presence of a suitable acid or base, alpha-hydroxyaldehydes, ketones, and imines can undergo isomerization that features the 1,2-shift of an alkyl or aryl group. In the process, the hydroxy group is converted to a carbonyl and the aldehyde/ketone or imine is converted to an alcohol or amine. Such alpha-ketol/alpha-iminol rearrangements are used in a wide variety of synthetic applications includ-ing asymmetric synthesis, tandem reactions, and the total synthesis and biosynthesis of natural products. This review explores the use of alpha-ketol rearrangements in these contexts over the past two decades.

Automated summary

This review examines the use of alpha-ketol rearrangements in various synthetic applications such as asymmetric synthesis, tandem reactions, and the total synthesis and biosynthesis of natural products over the past two decades.