Organoselenium-Catalyzed Asymmetric Cyclopropanations of (E)‑Chalcones

We report a new class of chiral tetrahydroselenophene based on (S)-diphenyl­(tetrahydroselenophen-2-yl)­methanol, which was prepared from (R)-3-(3-bromopropyl)-2,2-diphenyloxirane and sodium selenide. These chiral tetrahydroselenophene-based compounds were used to catalyze asymmetric cyclopropanatio...

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Bibliographic Details
Published inOrganic letters Vol. 23; no. 20; pp. 8104 - 8108
Main Authors Cheng, Pei-Tung, Tseng, Yu-Hsun, Chein, Rong-Jie
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.10.2021
Amer Chemical Soc
Subjects
Catalysis
Chalcones - chemical synthesis
Chalcones - chemistry
Chemistry
Chemistry, Organic
Cyclopropanes - chemistry
Molecular Structure
Organoselenium Compounds - chemistry
Physical Sciences
Science & Technology
FUNCTIONALIZATION
OXIDATION
ENANTIOSELECTIVE SYNTHESIS
MOLECULAR-STRUCTURE
SULFONIUM
VINYLCYCLOPROPANES
SELENIUM REAGENTS
SELENONIUM YLIDES
SULFUR
ALDEHYDES
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Summary:We report a new class of chiral tetrahydroselenophene based on (S)-diphenyl­(tetrahydroselenophen-2-yl)­methanol, which was prepared from (R)-3-(3-bromopropyl)-2,2-diphenyloxirane and sodium selenide. These chiral tetrahydroselenophene-based compounds were used to catalyze asymmetric cyclopropanation reactions; the selenonium ylide intermediates formed from these selenium-containing catalysts and benzyl bromide efficiently react with (E)-chalcones to give various cyclopropanes (27 examples) with excellent enantioselectivities of ≤99% ee and are the first examples of organoselenium-catalyzed asymmetric cyclopropanations.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c03243