Silver-Mediated Organic Transformations of Propargylamines to Enones, α-Thioketones, and Isochromans

Jian Fang Cui, Bin Yang, Qiong Yu, Nathanael Chun Him Lai, Han Chen, Man Kin Wong

Research output: Journal article publicationJournal articleAcademic researchpeer-review

1 Citation (Scopus)

Abstract

This work describes a series of silver-mediated transformations of propargylamines to provide diverse patterns of products, including enones, α-thioketones, and isochromans. A variety of enone derivatives were obtained by silver-catalyzed transformation of propargylamines with 3-chloroperoxybenzoic acid (m-CPBA) in aprotic solvent. In contrast, when the reactions were carried out in protic solvent with N-Boc-L-cysteine methyl ester (Boc = tert-butoxycarbonyl) as nucleophile, α-thioketones were obtained. Moreover, the first silver-mediated cascade cyclization of alkynyl alcohol-linked propargylamines giving isochroman scaffolds was also described in this paper.

Original languageEnglish
Pages (from-to)1476-1482
Number of pages7
JournalChemistrySelect
Volume4
Issue number4
DOIs
Publication statusPublished - 31 Jan 2019

Keywords

  • Enones
  • Isochromans
  • Propargylamines
  • Silver
  • Thioketones

ASJC Scopus subject areas

  • Chemistry(all)

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