期刊
ORGANIC LETTERS
卷 7, 期 14, 页码 2977-2980出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol050946j
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资金
- NIGMS NIH HHS [R01 GM071779] Funding Source: Medline
We report a one-step phosphine-catalyzed annulation between aldehydes and ethyl allenoate to form 6-substituted 2-pyrones. The mechanistic rationale for this reaction requires explicit discussion of the EIZ-isomerism of the zwitterionic intermediate formed by the addition of a phosphine to the allenoate. Sterically demanding trialkylphosphines facilitate the shift of equilibrium toward the E-isomeric zwitterion and lead to the formation of 6-substituted 2-pyrones. Various aromatic as well as aliphatic aldehydes undergo the transformation in moderate to excellent yield.
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