DAST-mediated ring-opening of cyclopropyl silyl ethers in nitriles: facile synthesis of allylic amides 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 in:Organic & biomolecular chemistry 2022-08, Vol.2 (33), p.6558-6561
Main Authors: Kirihara, Masayuki, Nakamura, Riho, Nakakura, Kana, Tujimoto, Kazuki, Salem, Mohamed S. H, Suzuki, Takeyuki, Takizawa, Shinobu
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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. 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%).
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00940d