Issue 2, 2021

Asymmetric synthesis of 9-alkyl tetrahydroxanthenones via tandem asymmetric Michael/cyclization promoted by chiral phosphoric acid

Abstract

A tandem asymmetric Michael-addition/cyclization of cyclic 1,3-dicarbonyl compounds to β,γ-unsaturated α-ketoesters catalyzed by chiral phosphoric acid is presented. This protocol provides a facile approach for the construction of enantioenriched 9-alkyl tetrahydroxanthenones, an ubiquitous framework found in a number of natural products and pharmaceutical molecules, in high yields with good to high enantioselectivities.

Graphical abstract: Asymmetric synthesis of 9-alkyl tetrahydroxanthenones via tandem asymmetric Michael/cyclization promoted by chiral phosphoric acid

Supplementary files

Article information

Article type
Communication
Submitted
25 Oct 2020
Accepted
30 Nov 2020
First published
09 Dec 2020

Org. Biomol. Chem., 2021,19, 348-354

Asymmetric synthesis of 9-alkyl tetrahydroxanthenones via tandem asymmetric Michael/cyclization promoted by chiral phosphoric acid

Y. Gao, Y. Hou, J. Chen, Y. Zhen, D. Xu, H. Zhang, H. Wei and W. Xie, Org. Biomol. Chem., 2021, 19, 348 DOI: 10.1039/D0OB02140G

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