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Silver‐Mediated Organic Transformations of Propargylamines to Enones, α‐Thioketones, and Isochromans
Author(s) -
Cui JianFang,
Yang Bin,
Yu Qiong,
Lai Nathanael ChunHim,
Chen Han,
Wong ManKin
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201900024
Subject(s) - nucleophile , solvent , chemistry , alcohol , organic solvent , organic chemistry , combinatorial chemistry , catalysis , chemical engineering , engineering
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.