Synthesis of Helical-Shaped Axially Chiral Bisoxime Ethers via Chiral Phosphoric-Acid-Catalyzed Sequential Enantioselective Condensations

A successful synthesis of helical-shaped axially chiral bisoxime ethers is reported. This approach utilized symmetric L-shaped diketone scaffolds as carbonyl components for the enantioselective condensation with hydroxylamines, delivering dual axially chiral oxime ethers with up to 99% ee. Additiona...

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Bibliographic Details
Published inOrganic letters Vol. 26; no. 13; pp. 2646 - 2650
Main Authors Shao, Bing-ru, Ren, Bai-hao, Jiang, Wen-feng, Shi, Lei
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.04.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CIRCULARLY-POLARIZED LUMINESCENCE
LIMITS
RECOGNITION
KINETIC RESOLUTION
DICHROISM
POLYMER
STEREOSELECTIVE SYNTHESES
ONE HUNDRED YEARS
COMPLEXATION
MOLECULES
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Summary:A successful synthesis of helical-shaped axially chiral bisoxime ethers is reported. This approach utilized symmetric L-shaped diketone scaffolds as carbonyl components for the enantioselective condensation with hydroxylamines, delivering dual axially chiral oxime ethers with up to 99% ee. Additionally, the axially chiral mono-oxime ethers of azabicyclic ketones with high ee’s were also successfully produced. Various chiral bicyclic lactams can be readily synthesized via Beckmann rearrangement, demonstrating a potential application in organic synthetic chemistry.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c00722