Homoconjugated ketones with extended unsaturation: Wavelength‐selective, regioselective, diastereoselective, and enantiospecific photochemical transformations of methyl 7‐oxospiro[5.5]undeca‐1,3‐and ‐2,4,‐diene‐2‐carboxylate

Jakob Oren, Michaela Vardi, Rossana Viskin, Sarah Abramson, Benzion Fuchs

Research output: Contribution to journalArticlepeer-review

Abstract

The title molecules were shown to photorearrange with remarkable selectivity. Wavelength variation steers the rearrangement modes, of which the [1,2]‐acyl shift was found to be largely regioselective, diastereoselective, and enantiospecific. Chemical intercorrelation of products and mechanistic studies were carried out all along. The potential significance of these photochemical processes in selective synthetic schemes is discussed.

Original languageEnglish
Pages (from-to)1182-1193
Number of pages12
JournalHelvetica Chimica Acta
Volume76
Issue number3
DOIs
StatePublished - 12 May 1993

Fingerprint

Dive into the research topics of 'Homoconjugated ketones with extended unsaturation: Wavelength‐selective, regioselective, diastereoselective, and enantiospecific photochemical transformations of methyl 7‐oxospiro[5.5]undeca‐1,3‐and ‐2,4,‐diene‐2‐carboxylate'. Together they form a unique fingerprint.

Cite this