Chemical Communications 2012-07-11

Asymmetric transformations involving 1,2-dicarbonyl compounds as pronucleophiles.

Wilfried Raimondi, Damien Bonne, Jean Rodriguez

Index: Chem. Commun. (Camb.) 48(54) , 6763-75, (2012)

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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.