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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

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

Jakkampudi Satish S Parella Ramarao R Zhao John C-G JC

Organic & biomolecular chemistry 20181201 1

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 h ...[more]

PMID: 30525178

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