TEMPO-Catalyzed Oxidation of 3‑O‑Benzylated/Silylated Glycals to the Corresponding Enones Using a PIFA–Water Reagent System

A simple, highly efficient and regiospecific method for the direct conversion of 3-O-benzylated as well as silylated glycals into the corresponding enones has been developed using PIFA–TEMPO and water reagent system. The reaction is scalable on a gram scale under mild conditions with a yield up to 8...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 83; no. 17; pp. 10535 - 10540
Main Authors Chennaiah, Ande, Verma, Ashish Kumar, Vankar, Yashwant D
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.09.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OLIGOSACCHARIDES
TRIISOPROPYLSILYL ENOL ETHERS
ANALOGS
N-GLYCOPEPTIDES
CHEMISTRY
SUGARS
TRIMETHYLSILYL AZIDE
CONJUGATE ADDITIONS
HYPERVALENT IODINE REAGENTS
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Summary:A simple, highly efficient and regiospecific method for the direct conversion of 3-O-benzylated as well as silylated glycals into the corresponding enones has been developed using PIFA–TEMPO and water reagent system. The reaction is scalable on a gram scale under mild conditions with a yield up to 86%.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b01191