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Issue 2, 2021
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Asymmetric synthesis of 9-alkyl tetrahydroxanthenones via tandem asymmetric Michael/cyclization promoted by chiral phosphoric acid

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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

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Article information


Submitted
25 Oct 2020
Accepted
30 Nov 2020
First published
09 Dec 2020

Org. Biomol. Chem., 2021,19, 348-354
Article type
Communication

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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