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

Cui, Jian-Fang1,3; Yang, Bin1; Yu, Qiong2; Lai, Nathanael Chun-Him1; Chen, Han1; Wong, Man-Kin1,2

2019-01-31

10.1002/slct.201900024

ChemistrySelect   影响因子和分区

2365-6549

This work describes a series of silver-mediated transformations of propargylamines to provide diverse patterns of products, including enones, alpha-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, alpha-thioketones were obtained. Moreover, the first silver-mediated cascade cyclization of alkynyl alcohol-linked propargylamines giving isochroman scaffolds was also described in this paper.

Enones Isochromans Propargylamines Silver Thioketones

SCI

英语

其他

Southern University of Science and Technology[Y01216234]

Chemistry

Chemistry, Multidisciplinary

WOS:000457441400052

WILEY-V C H VERLAG GMBH

Web of Science

1.Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, State Key Lab Chem Biol & Drug Discovery, Hong Kong, Peoples R China
2.Hong Kong Polytech Univ, Shenzhen Res Inst, Shenzhen, Peoples R China
3.Southern Univ Sci & Technol, Dept Chem, Shenzhen, Peoples R China

Cui, Jian-Fang,Yang, Bin,Yu, Qiong,et al. Silver-Mediated Organic Transformations of Propargylamines to Enones, alpha-Thioketones, and Isochromans[J]. ChemistrySelect,2019,4(4):1476-1482.

Cui, Jian-Fang,Yang, Bin,Yu, Qiong,Lai, Nathanael Chun-Him,Chen, Han,&Wong, Man-Kin.(2019).Silver-Mediated Organic Transformations of Propargylamines to Enones, alpha-Thioketones, and Isochromans.ChemistrySelect,4(4),1476-1482.

Cui, Jian-Fang,et al."Silver-Mediated Organic Transformations of Propargylamines to Enones, alpha-Thioketones, and Isochromans".ChemistrySelect 4.4(2019):1476-1482.