Issue 21, 2021

Stereoselective benzilic acid rearrangements: new advances on an old story

Abstract

The benzilic acid rearrangement (BAR) is the oldest rearrangement on record. It is a powerful synthetic tool for accessing significant biologically active molecules. The reaction is both catalytic (generally Lewis acid) and stereoselective, recently the first catalytic asymmetric version was reported with astonshing results (ees of up to 97%) to give chiral tartronic esters. In this unique highlight, we look at the progress made over the last 10 years on the stereoseletive aspects of this synthetic transformation, showing interesting examples of this rearrangment in both acyclic and cyclic systems (like for instance its importance in the stereoselective synthesis of syn and anti-hydroxy-iso-evoninic acids, α-hydroxy-α-perfluoroalkyl esters, a selective nonsteroidal mineralocorticoid receptor antagonist, Geldanamycin type polyketides and (−)-isatisine A, etc.) and the differnces in stereoselectivity encountered which culminated recently in the conquest of the first catalytic asymmetric example on record.

Graphical abstract: Stereoselective benzilic acid rearrangements: new advances on an old story

Article information

Article type
Highlight
Submitted
04 Dec 2020
Accepted
05 Feb 2021
First published
22 Feb 2021

Chem. Commun., 2021,57, 2585-2590

Stereoselective benzilic acid rearrangements: new advances on an old story

A. J. Burke and A. Moutayakine, Chem. Commun., 2021, 57, 2585 DOI: 10.1039/D0CC07905G

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