DAST-mediated ring-opening of cyclopropyl silyl ethers in nitriles: facile synthesis of allylic amides via a Ritter-type process

A diethylaminosulfur trifluoride (DAST)-mediated ring-opening reaction of cyclopropyl silyl ethers in nitriles produced allylic amides in moderate to good yields (up to 87%). Time course studies using ReactIR and O-isotopic labeling mechanistic studies suggested that the present reaction occurs via...

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Published inOrganic & biomolecular chemistry Vol. 20; no. 33; pp. 6558 - 6561
Main Authors Kirihara, Masayuki, Nakamura, Riho, Nakakura, Kana, Tujimoto, Kazuki, Salem, Mohamed S. H., Suzuki, Takeyuki, Takizawa, Shinobu
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 24.08.2022
Royal Society of Chemistry
Subjects
Amides
Chemistry
Chemistry, Organic
Cyanides
Ethers
Isotopic labeling
Nitriles
Organic compounds
Physical Sciences
Radioactive labeling
Ring opening
Science & Technology
ACID
FRAGMENTATION
CLEAVAGE
TERTIARY
DIETHYLAMINOSULFUR TRIFLUORIDE
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Summary:A diethylaminosulfur trifluoride (DAST)-mediated ring-opening reaction of cyclopropyl silyl ethers in nitriles produced allylic amides in moderate to good yields (up to 87%). Time course studies using ReactIR and O-isotopic labeling mechanistic studies suggested that the present reaction occurs via a Ritter-type process, leading to the formation of allylic amides.
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ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00940d