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.
A New Organocatalytic Concept for Asymmetric α-Alkylation of Aldehydes / Lorenzo Caruana;Florian Kniep;Tore Kiilerich Johansen;Pernille H. Poulsen;Karl Anker Jørgensen. - In: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. - ISSN 0002-7863. - STAMPA. - 136:(2014), pp. 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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
