Stereoselective synthesis of enynones via base-catalyzed isomerization of 1,5-disubstituted-2,4-pentadiynyl silyl ethers or their alcohol derivatives.
1,5-Disubstituted-2,4-pentadiynyl silyl ethers undergo smooth desilylative isomerization to afford cis-enynones as major products with moderate stereoselectivities in the presence of a catalytic amount of KO(t)Bu or DBU. While the isomerization reactions of their alcohol derivatives catalyzed by KOH, KO(t)Bu or NaH take place efficiently to produce trans-enynones with high stereoselectivities. These reactions provide convenient and practical routes for the synthesis of enynones with a wide range of substitution groups.
Chen
Jingjin
J
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, People's Republic of China.
Fan
Guoqin
G
Liu
Yuanhong
Y