Asymmetric transformations involving 1,2-dicarbonyl compounds as pronucleophiles.
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.
Aix-Marseille Université, UMR CNRS 7313 iSm2, Centre Saint Jérôme, service 531, 13397 Marseille, France.
Wilfried
W
Raimondi
Damien
D
Bonne
Jean
J
Rodriguez
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D009532:Nickel / Q000737:chemistry; D007652:Oxo-Acid-Lyases / Q000378:metabolism; D013237:Stereoisomerism
D000447:Aldehydes; D007659:Ketones; D009532:Nickel; D007652:Oxo-Acid-Lyases; C018728:N-acetylneuraminate lyase