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Stereoselective synthesis of chromane derivatives via a domino reaction catalyzed by modularly designed organocatalysts

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Abstract

A highly enantio- and diastereoselective method for the synthesis of functionalized chroman-2-ones and chromanes was achieved by using an organocatalytic domino Michael/hemiacetalization reaction of aliphatic aldehydes and (E)-2-(2-nitrovinyl)phenols followed by a PCC oxidation and dehydroxylation, respectively. Using the modularly designed organocatalysts (MDOs) self-assembled from cinchona alkaloid derivatives and amino acids in the reaction media, the title products were obtained in good to high yields (up to 97%) and excellent diastereoselectivities (up to 99 : 1 dr) and enantioselectivities (up to 99% ee).

Graphical abstract: Stereoselective synthesis of chromane derivatives via a domino reaction catalyzed by modularly designed organocatalysts

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Publication details

The article was received on 29 Oct 2018, accepted on 03 Dec 2018 and first published on 06 Dec 2018


Article type: Paper
DOI: 10.1039/C8OB02677G
Citation: Org. Biomol. Chem., 2019, Advance Article
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    Stereoselective synthesis of chromane derivatives via a domino reaction catalyzed by modularly designed organocatalysts

    S. Jakkampudi, R. Parella and J. C.-G. Zhao, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C8OB02677G

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