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).
|Number of pages||11|
|Publication status||Published - 2017|
ASJC Scopus subject areas
- Analytical Chemistry
- Organic Chemistry