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Author Wang, Chang‐Sheng ♦ Roisnel, Thierry ♦ Dixneuf, Pierre H. ♦ Soulé, Jean-François
Source Hyper Articles en Ligne (HAL)
Content type Text
Publisher Wiley-VCH Verlag
File Format PDF
Language English
Subject Keyword Radical reaction ♦ Cascade ♦ Heterocycles ♦ Ketones ♦ Peroxides ♦ chim ♦ Chemical Sciences/Catalysis
Abstract Azaspiro[4.5]trienones bearing ketone side chains at the 3-position are prepared from N-alkyl-arylpropiolamides and ketones via oxidative 1,2-difunctionalization of alkynes. The cascade sequence starts with the generation of alkenyl peroxide intermediates, which are obtained by addition of tert-butyl hydroperoxide to ketones in presence of a catalytic amount of a strong acid. Then, the ketone radical adds to alkynes, followed by spirocyclization and dearomatization process. This method represents a new example of difunctionalization of alkynes with simultaneous formation of two carbon-carbon single bonds and one carbon-oxygen double bond in one step.
ISSN 16154150
Educational Use Research
Learning Resource Type Article
Publisher Date 2018-12-07
e-ISSN 16154169
Journal Advanced Synthesis and Catalysis
Volume Number 360
Page Count 7
Starting Page 1
Ending Page 7