K(2)CO(3)-catalyzed Michael addition-lactonization reaction of 1,2-allenyl ketones with electron-withdrawing group substituted acetates. An efficient synthesis of alpha-pyrone derivatives.
[reaction: see text] Alpha-pyrone derivatives were synthesized via the base catalyzed or promoted reaction of 1,2-allenyl ketones and electron-withdrawing group substituted acetates. The reaction was believed to proceed through a Michael addition C-C double-bond migration-lactonization process.
Ma
Shengming
S
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, PR China. masm@pub.sioc.ac.cn
Yin
Shaohu
S
Li
Lintao
L
Tao
Fenggang
F
D000085:Acetates / Q000737:chemistry; D002254:Carbonates; D002384:Catalysis; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis; D011188:Potassium; D011753:Pyrones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000085:Acetates; D002254:Carbonates; D007202:Indicators and Reagents; D007659:Ketones; D007783:Lactones; D011753:Pyrones; C037593:potassium carbonate; D011188:Potassium