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

Shengming Ma; Shaohu Yin; Lintao Li; Fenggang Tao

doi:10.1021/ol0170859

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

Org Lett. 2002 Feb 21;4(4):505-7. doi: 10.1021/ol0170859.

Authors

Shengming Ma¹, Shaohu Yin, Lintao Li, Fenggang Tao

Affiliation

¹ 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

PMID: 11843577
DOI: 10.1021/ol0170859

Abstract

[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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetates / chemistry
Carbonates
Catalysis
Indicators and Reagents
Ketones / chemistry
Lactones / chemical synthesis
Potassium
Pyrones / chemical synthesis*
Stereoisomerism

Substances

Acetates
Carbonates
Indicators and Reagents
Ketones
Lactones
Pyrones
potassium carbonate
Potassium