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  • Title: Stereoselective synthesis of chromane derivatives via a domino reaction catalyzed by modularly designed organocatalysts.
    Author: Jakkampudi S, Parella R, Zhao JC.
    Journal: Org Biomol Chem; 2018 Dec 19; 17(1):151-155. PubMed ID: 30525178.
    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).
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