An intramolecular nucleophile-catalyzed aldollactonization (ncal) reaction of s-Aryl-(e)-6-oxohex-2-enethioate with n,n-4-dimethylaminopyridine N-oxide

Hiroki Mandai, Keita Shimowaki, Kohei Hongo, Koichi Mitsudo, Seiji Suga

Research output: Contribution to journalArticle

Abstract

We have developed an intramolecular nucleophile-catalyzed aldollactonization (NCAL) reaction of S-Aryl-(E)-6-oxohex-2-enethiolate with N,N-4-dimethylaminopyridine N-oxide (DMAPO) to afford densely functionalized bicyclic β-lactones in moderate yield. This unique transformation may be explained in terms of nucleophilic substitution of the S-Aryl moiety by DMAPO, followed by 1,4-Addition of aryl thiolate to generate a zwitterionic enolate and an intramolecular C-C bond-forming reaction (aldol-lactonization).

Original languageEnglish
Pages (from-to)492-502
Number of pages11
JournalHeterocycles
Volume94
Issue number3
DOIs
Publication statusPublished - 2017

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Nucleophiles
Oxides
Lactones
Substitution reactions
4-dimethylaminopyridine
4-N,N-dimethylaminopyridine
3-hydroxybutanal

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

An intramolecular nucleophile-catalyzed aldollactonization (ncal) reaction of s-Aryl-(e)-6-oxohex-2-enethioate with n,n-4-dimethylaminopyridine N-oxide. / Mandai, Hiroki; Shimowaki, Keita; Hongo, Kohei; Mitsudo, Koichi; Suga, Seiji.

In: Heterocycles, Vol. 94, No. 3, 2017, p. 492-502.

Research output: Contribution to journalArticle

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