Asymmetric Synthesis of Cyclohexenone-Fused Isochromans via Quinidine-Catalyzed Domino Peroxyhemiacetalization/Oxa-Michael Addition/Desymmetrization Sequence

A highly enantio- and diastereoselective synthesis of highly functionalized isochromans was achieved through an organocatalyzed domino reaction. Quinidine as the catalyst initiates a peroxyhemiacetalization/oxa-Michael/desymmetrization domino sequence between various 2,5-cyclohexadienone-tethered ar...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 87; no. 9; pp. 6397 - 6402
Main Authors Tamanna, Hussain, Yaseen, Sharma, Deepak, Chauhan, Pankaj
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.05.2022
Amer Chemical Soc
Subjects
Aldehydes
Catalysis
Chemistry
Chemistry, Organic
Physical Sciences
Quinidine
Science & Technology
Stereoisomerism
CASCADE
ROOTS
ENANTIOSELECTIVE SYNTHESIS
TRANSFORMATIONS
COMPLEXITY
DESYMMETRIZATION
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Summary:A highly enantio- and diastereoselective synthesis of highly functionalized isochromans was achieved through an organocatalyzed domino reaction. Quinidine as the catalyst initiates a peroxyhemiacetalization/oxa-Michael/desymmetrization domino sequence between various 2,5-cyclohexadienone-tethered aryl aldehydes with hydroperoxides to generate the single diastereomers of isochromans appended with a cyclohexenone ring bearing three vicinal stereocenters in good yields and high enantioselectivities under ambient reaction conditions.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00215