Mitsunobu C-Alkylation of Meldrum's Acids

Tony Kung Ming Shing, Lian Hai Li, Ke Savaram Narkunan

Research output: Contribution to journalArticle

31 Citations (Scopus)

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
Externally publishedYes

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Alkylation
Bearings (structural)
Carbon
Regioselectivity
Alkylating Agents
Dehydration
Catalysts
Meldrum's acid
allyl alcohol

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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.

Mitsunobu C-Alkylation of Meldrum's Acids. / Shing, Tony Kung Ming; Li, Lian Hai; Narkunan, Ke Savaram.

In: Journal of Organic Chemistry, Vol. 62, No. 6, 01.12.1997, p. 1617-1622.

Research output: Contribution to journalArticle

Shing, TKM, Li, LH & Narkunan, KS 1997, 'Mitsunobu C-Alkylation of Meldrum's Acids', Journal of Organic Chemistry, vol. 62, no. 6, pp. 1617-1622.
Shing TKM, Li LH, Narkunan KS. Mitsunobu C-Alkylation of Meldrum's Acids. Journal of Organic Chemistry. 1997 Dec 1;62(6):1617-1622.
Shing, Tony Kung Ming ; Li, Lian Hai ; Narkunan, Ke Savaram. / Mitsunobu C-Alkylation of Meldrum's Acids. In: Journal of Organic Chemistry. 1997 ; Vol. 62, No. 6. pp. 1617-1622.
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