DAST-mediated ring-opening of cyclopropyl silyl ethers in nitriles: facile synthesis of allylic amides via a Ritter-type process. Issue 33 (28th July 2022)

• Record Type: Journal Article
• Authors: Kirihara, Masayuki; Nakamura, Riho; Nakakura, Kana; Tujimoto, Kazuki; Salem, Mohamed S. H.; Suzuki, Takeyuki; Takizawa, Shinobu
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 33(2022)
• Page Start: 6558
• Page End: 6561
• Publication Date: 2022-07-28
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob00940d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : 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%). Abstract : 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.