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A Rapid Entry to Diverse γ‐Ylidenetetronate Derivatives through Regioselective Bromination of Tetronic Acid Derived γ‐Lactones and Metal‐Catalyzed Postfunctionalization
Author(s) -
Chopin Nicolas,
Yanai Hikaru,
Iikawa Shinya,
Pilet Guillaume,
Bouillon JeanPhilippe,
Médebielle Maurice
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500663
Subject(s) - sonogashira coupling , chemistry , stille reaction , halogenation , regioselectivity , aryl , cycloaddition , catalysis , organic chemistry , azide , palladium , medicinal chemistry , combinatorial chemistry , alkyl
The synthesis of a series of diverse methyl and benzyl γ‐ylidenetetronate derivatives was accomplished through the condensation of methyl and benzyl tetronates with (hetero)aryl aldehydes in a new two‐ or three‐step aldolisation/dehydration sequence. The bromination of methyl and benzyl γ‐ylidenetetronates occurred under mild conditions to provide the corresponding C‐3‐brominated γ‐unsaturated lactones. Di‐ and tribrominated γ‐lactones were prepared under slightly different conditions. Some brominated materials were employed in representative Stille, Suzuki–Miyaura, and Sonogashira cross‐coupling reactions to yield functionalized methyl and benzyl γ‐ylidenetetronate derivatives. Compounds that resulted from the Sonogashira cross‐coupling reactions were desilylated and converted into 1,2,3‐triazole derivatives through a copper(I)‐catalyzed 1,3‐dipolar cycloaddition reaction with benzyl azide.