| Autor: |
Cui, Jian‐Fang, Yang, Bin, Yu, Qiong, Lai, Nathanael Chun‐Him, Chen, Han, Wong, Man‐Kin |
| Předmět: |
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| Zdroj: |
ChemistrySelect; 1/31/2019, Vol. 4 Issue 4, p1476-1482, 7p |
| Abstrakt: |
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. A series of silver‐mediated synthetic strategies for propargylamines to build molecular complexity which provided a variety of structural scaffolds including enones, α‐thioketones, and isochromans have been developed. Propargylic amine N‐oxides generated in situ from the corresponding propargylamines through oxidation were converted to enones in aprotic solvent by silver catalysis, and α‐thioketones were obtained by using protic solvent. Silver‐mediated transformation of alkynyl alcohol‐linked propargylamines provided isochromans. [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
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