Issue 54, 2012

Asymmetric transformations involving 1,2-dicarbonyl compounds as pronucleophiles

Abstract

This article concentrates on the versatile nucleophilic reactivity of 1,2-dicarbonyl compounds in various asymmetric transformations. Although underexploited in comparison to their 1,3-dicarbonyl homologues, the presence of adjacent multiple reactive centres allows the selection of specific activation modes for enhancing the reactivity of these important ambident pronucleophiles. They can be involved in selective formation of C–C, C–O or C–N bonds leading to various optically active targets in the acyclic and cyclic series including three- to seven-membered ring systems. Recent contributions in the field of biochemical, organometallic and organic catalytic transformations as well as some relevant stoichiometric approaches are discussed from synthetic and mechanistic point of views highlighting some important stereochemical issues.

Graphical abstract: Asymmetric transformations involving 1,2-dicarbonyl compounds as pronucleophiles

  • This article is part of the themed collection: Chirality

Article information

Article type
Feature Article
Submitted
31 Jan 2012
Accepted
24 Apr 2012
First published
25 Apr 2012

Chem. Commun., 2012,48, 6763-6775

Asymmetric transformations involving 1,2-dicarbonyl compounds as pronucleophiles

W. Raimondi, D. Bonne and J. Rodriguez, Chem. Commun., 2012, 48, 6763 DOI: 10.1039/C2CC30691C

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