Synthesis p. 130 - 132 (1986)
Update date:2022-07-29
Topics: Organocatalysis Biocatalysis Radical Chemistry Photochemistry Flow Chemistry Chiral Ligand-Free Approaches Cooperative Catalysis
Maruoka, Keiji
Nakai, Shuichi
Sakurai, Minoru
Yamamoto, Hisashi
A new approach has been demonstrated for the asymmetric synthesis of α-substituted carbonyl compounds.Thus, the key assymetric carbon-carbon bond formation is accomplished by the highly diastereoselective addition of organoaluminum reagents to the chiral α,β-unsaturated acetal derived from the α,β-unsaturated aldehyde and (R,R)-tartaric acid diamide to furnish the 1,4-adduct preferentially along with the 1,2-adduct as a minor product.Subsequent oxidation of the combined adducts with ozone or the system potassium permanganate/sodium periodate gives rise to the optically active α-substituted aldehyde, ketone, or carboxylic acid, respectively, with high enantioselectivities.The present method has been applied to the facile synthesis of an anti-inflammatory agent and the principal alarm pheromone of the leaf-cutting ant Atta texana in optically active forms.
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