Synthetic applications of chiral 1,3-dioxolan-4-ones and 3-acyloxazolidin-5-ones

Robert Alan Aitken, Steven Derek McGill, Lynn Anita Power

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

Chiral dioxolanones derived from alpha-hydroxy acids can act as chiral acyl anion equivalents for addition to ethyl crotonate, nitroalkenes and butenolide. Subsequent flash vacuum pyrolysis results in loss of CO and (BuCHO)-C-t to give products. The related N-acyl and N-thioacyl-1,3-oxazolidin-5-ones formed from alpha-amino acids behave in a quite different way with loss of CO2 upon pyrolysis leading via N-(thio) acylaziridines to oxazolines and thiazolines. The stereochemistry of these transformations, both relative and absolute, is discussed and a mechanism involving an azomethine carboxylate intermediate is proposed.

Original languageEnglish
Pages (from-to)293-300
Number of pages8
JournalARKIVOC
Volume7
Issue numbervii
Publication statusPublished - 2006

Keywords

  • dioxolanones
  • acyl-anion
  • oxazolidiones
  • acylaziridines
  • oxazolines
  • thiazolines
  • FLASH VACUUM PYROLYSIS
  • ACID

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