The organocatalytic asymmetric α-alkylation of aldehydes by 1,6-conjugated addition of enamines to p-quinone methides is described. Employing a newly developed class of chiral secondary amine catalysts, α- diarylmethine-substituted aldehydes with two contiguous stereocenters have been synthesized in a simple manner with good diastereocontrol and excellent enantioselectivity.
Lorenzo Caruana, Florian Kniep, Tore Kiilerich Johansen, Pernille H. Poulsen, Karl Anker Jørgensen (2014). A New Organocatalytic Concept for Asymmetric α-Alkylation of Aldehydes. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 136, 15929-15932 [10.1021/ja510475n].
A New Organocatalytic Concept for Asymmetric α-Alkylation of Aldehydes
CARUANA, LORENZO;
2014
Abstract
The organocatalytic asymmetric α-alkylation of aldehydes by 1,6-conjugated addition of enamines to p-quinone methides is described. Employing a newly developed class of chiral secondary amine catalysts, α- diarylmethine-substituted aldehydes with two contiguous stereocenters have been synthesized in a simple manner with good diastereocontrol and excellent enantioselectivity.File in questo prodotto:
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