Development of novel diastereoselective alkenylation of enolates using alkenylselenonium salts.
[reaction: see text] A novel alkenylation of enolates using alkenylselenonium salts is described. A reaction of lithium enolates, which were prepared in situ by the reaction of LiHMDS and carbonyl compounds, with alkenylselenonium salts gave the ethenylation products of carbonyl compounds in high yield. Diastereoselective alkenylation was also accomplished by the reaction of the enolates derived from N-acyl-1,3-oxazolidin-2-ones with the alkenylselenonium salt to afford good results (up to 92% yield and up to 95% de).
Watanabe
Shin-Ichi
S
Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan.
Ikeda
Takahiro
T
Kataoka
Tadashi
T
Tanabe
Genzoh
G
Muraoka
Osamu
O