Double deprotonation of acetylenic oxiranes: synthesis of allenic ketones through Dilithio Ynenolates.
[reaction: see text] The double deprotonation of acetylenic oxiranes gives allenic ketones through the 1,2-H or 1,2-Ar shift on the transient oxiranyl dianion intermediates. The resulting dilithium ynenolates give allenic ketones upon hydrolysis or can be quenched with various electrophiles.
Denichoux
Aurélien
A
Laboratoire de Chimie Organique, UMR 7611, Bte courrier 183, Université Pierre et Marie Curie, 4 place Jussieu, 75252 Paris Cedex 05, France.
Ferreira
Franck
F
Chemla
Fabrice
F