Mitsunobu C-Alkylation of Meldrum's Acids

Tony K.M. Shing, Lian Hai Li, Ke Savaram Narkunan

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Abstract

C-Dialkylation of Meldrum's acid (2a) and 5-benzyl Meldrum's acid (2b) can be achieved through Mitsunobu dehydration using allylic and arylmethyl alcohols as alkylating agents. This is the first time that the Mitsunobu reaction is successfully applied to the C-alkylation of a highly enolizable cyclic β-dicarbonyl system. With primary (allylic and arylmethyl) alcohols, the alkylations always take place at the carbon bearing the hydroxy group. For secondary allylic alcohols, a catalytic amount of Pd(0) must be added to enhance the regioselectivity of C-alkylation over O-alkylation. With (Ph3P)4Pd(0) as a catalyst, the reaction occurs specifically at the less hindered carbon, and the configuration of the resultant double bond is always trans. Attempts to monoalkylate Meldrum's acids 2a and 2b failed.

Original languageEnglish
Pages (from-to)1617-1622
Number of pages6
JournalJournal of Organic Chemistry
Volume62
Issue number6
Publication statusPublished - 1997 Dec 1

ASJC Scopus subject areas

  • Organic Chemistry

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    Shing, T. K. M., Li, L. H., & Narkunan, K. S. (1997). Mitsunobu C-Alkylation of Meldrum's Acids. Journal of Organic Chemistry, 62(6), 1617-1622.