[2+2]-Photocycloaddition reactions of tetronic acid esters and amides

Jörg P. Hehn, Diego Gamba-Sánchez, Michael Kemmler, Martin Fleck, Birte Basler, Thorsten Bach

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Tetronic acid esters and amides, which are readily available from the corresponding tetronic acids, serve as useful starting materials in an intra- or intermolecular [2+2]-photocycloaddition reaction. Typical reaction conditions are irradiation at λ =254 nm in diethyl ether or an alcohol as the solvent. The bi-, tri- or tetracyclic products so obtained can be further utilized by ring opening either of the lactone or the cyclobutane ring. Lactone ring opening led to the use of a tetramide photocycloaddition product as a conformationally restricted β -proline analogue and to an application of a tetronate photocycloaddition product in the total synthesis of punctaporonin C.

Original languageEnglish
Article numberC01610SS
Pages (from-to)2308-2312
Number of pages5
JournalSynthesis
Issue number13
DOIs
StatePublished - 2010

Keywords

  • [2+2] cycloadditions
  • cyclobutanes
  • diastereoselectivity
  • heterocycles
  • photochemistry

Fingerprint

Dive into the research topics of '[2+2]-Photocycloaddition reactions of tetronic acid esters and amides'. Together they form a unique fingerprint.

Cite this