Highly enantioselective addition of aliphatic aldehydes to 2-hydroxychalcone enabled by cooperative organocatalysts.

Highly enantioselective addition of aliphatic aldehydes to 2-hydroxychalcone enabled by cooperative organocatalysts.
Chem Commun (Camb). 2020 Jul 29;:
Authors: Hu J, Gao YQ, Xu D, Chen L, Wen W, Hou Y, Chen L, Xie W
Abstract
Herein, we developed an enantioselective addition of aliphatic aldehydes to 2-hydroxychalcone promoted by cooperative organocatalysts, giving access to hybrid flavonoids in excellent enantioselectivities. This reaction took advantage of cycloisomerization of 2-hydroxychalcone to form a transient flavylium under the irradiation of 24 W CFL, which was trapped by the in situ generated chiral enamine intermediate. The synergistic action of chiral phosphoric acid secured the excellent outcome of this reaction by ion-pairing with the transient flavylium.
PMID: 32724997 [PubMed - as supplied by publisher]

Source: Chemical Communications - July 28, 2020 Category: Chemistry Authors: Hu J, Gao YQ, Xu D, Chen L, Wen W, Hou Y, Chen L, Xie W Tags: Chem Commun (Camb) Source Type: research