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Synthesis 1996; 1996(2): 215-218
DOI: 10.1055/s-1996-4201
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Synthesis and Utility of a Novel Methylene Meldrum’s Acid Precursor

Mohammad Zia-Ebrahimi* , George W. Huffman
  • *Infectious Disease Research, Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 46285, USA, Fax +1(317)2772035; E-mail MZE@LILLY.COM
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Publication History

Publication Date:
31 December 2000 (online)

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The betaine 1-[(6-hydroxy-2,2-dimethyl-4-oxo-4H-1,3-dioxin-5-yl)-methyl]pyridinium hydroxide, inner salt (1), a pyridine adduct of methylene Meldrum’s acid is a stable source of methylene Meldrum’s acid. It is a versatile reagent which enhances the yields of Diels-Alder and Michael reactions when used instead of traditional methods that generate methylene Meldrum’s acid in situ. Diels-Alder reactions performed with this reagent provide products in essentially quantitative yields. Michael reactions result in products in excess of 70% yield. This reagent provides a useful synthetic route to γ-carboxyglutamic acid.

methylene Meldrum’s acid - γ-carboxyglutamic acid - betaine - Diels-Alder - Michael addition

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