Double deprotonation of acetylenic oxiranes: synthesis of allenic ketones through Dilithio Ynenolates

Org Lett. 2004 Sep 30;6(20):3509-12. doi: 10.1021/ol048630j.

Abstract

[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.