Beilstein J. Org. Chem.2021,17, 2570–2584, doi:10.3762/bjoc.17.172
, tandem reactions, and the total synthesis and biosynthesis of natural products. This review explores the use of α-ketol rearrangements in these contexts over the past two decades.
Keywords: acyloin rearrangement; asymmetric synthesis; iminolrearrangement; ketol rearrangement; tandem reactions
compounds; or (4) the use of imines (X = NR′′), which lead to more stable α-amino ketones.
The α-ketol or α-iminolrearrangement is a synthetic organic tool used for ring expansions and contractions and other isomerizations that is also used in some biological pathways [2][3]. Works featuring these
sulfuric acid, no 102 was formed, only the free alcohol (103) in 56% yield (Figure 19c). As an extension of this method, the authors demonstrated the formation of 105, an analogue of the anesthetic ketamine (106), in 83% yield using silica gel (Figure 19d) [29].
An α‑iminolrearrangement was utilized by
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Graphical Abstract
Figure 1:
Generalized α-ketol or α-iminol rearrangement.