Issue 33, 2017

Advances in chemoselective intermolecular cross-benzoin-type condensation reactions

Abstract

The intermolecular cross-benzoin and acyloin condensation reactions are powerful approaches to α-hydroxy carbonyls in a single step. However, their potentiality suffers from the occurrence of side reactions including self-condensation and the formation of the undesired cross-acyloin. The broad range of azolium salt precatalysts available confers high tunability to NHC mediated benzoin condensation, assuring a good level of selectivity to the direct coupling between two non-equivalent aldehydes. Many efforts have also been devoted to the design of strategies that expand the range of suitable reaction partners beyond the traditional aldehydes and to the discovery of novel umpolung catalytic systems. The synthesis of both racemic and enantiomerically enriched acyloins is reviewed.

Graphical abstract: Advances in chemoselective intermolecular cross-benzoin-type condensation reactions

Article information

Article type
Review Article
Submitted
06 Maw 2017
Accepted
31 Maw 2017
First published
31 Maw 2017

Org. Biomol. Chem., 2017,15, 6867-6887

Advances in chemoselective intermolecular cross-benzoin-type condensation reactions

N. Gaggero and S. Pandini, Org. Biomol. Chem., 2017, 15, 6867 DOI: 10.1039/C7OB01662J

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