Strain-driven direct cross-aldol and -ketol reactions of four-membered heterocyclic ketones

Zoltán Dobi, Tamás Holczbauer, T. Soós

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Owing to the ring strain and α-heteroatom effect, the four-membered heterocyclic ketones can undergo direct cross-aldol and -ketol reactions without the need for preformed enol or "enolate-like" intermediates. Besides the organocatalyzed cross-ketol addition onto their highly active carbonyl group, their ability to act as a nucleophilic donor has also been explored. As a result, a number of discrete aldol adducts were synthesized and the distinct reactivities were successfully combined into a double-aldol one-pot reaction.

Original languageEnglish
Pages (from-to)2634-2637
Number of pages4
JournalOrganic Letters
Volume17
Issue number11
DOIs
Publication statusPublished - Jun 5 2015

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Ketones
ketones
adducts
reactivity
rings
3-hydroxybutanal

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry
  • Medicine(all)

Cite this

Strain-driven direct cross-aldol and -ketol reactions of four-membered heterocyclic ketones. / Dobi, Zoltán; Holczbauer, Tamás; Soós, T.

In: Organic Letters, Vol. 17, No. 11, 05.06.2015, p. 2634-2637.

Research output: Contribution to journalArticle

Dobi, Zoltán ; Holczbauer, Tamás ; Soós, T. / Strain-driven direct cross-aldol and -ketol reactions of four-membered heterocyclic ketones. In: Organic Letters. 2015 ; Vol. 17, No. 11. pp. 2634-2637.
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