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

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).

SUBMITTER: Jakkampudi S 

PROVIDER: S-EPMC6317902 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature