Enantioselective photochemical reactions of 2-pyridones in solution

Thorsten Bach, Hermann Bergmann, Klaus Harms

Research output: Contribution to journalArticlepeer-review

66 Scopus citations

Abstract

(Matrix presented) Two key photochemical reactions of prochiral 2-pyridones were studied in the presence of a chiral host. The [4 + 4]-photocycloaddition with cyclopentadiene (CpH) proceeded smoothly and with high enantioselectivity (84-87% ee). The absolute configuration of the endo-diastereoisomer was established by X-ray crystallography. The electrocyclic [4π]-ring closure to 3-oxo-2-azabicyclo[2.2.0]-5-hexenes occurred with lower enantioselectivity (20-23% ee at -20°C). The velocity of the latter reaction slowed significantly with decreasing temperature.

Original languageEnglish
Pages (from-to)601-603
Number of pages3
JournalOrganic Letters
Volume3
Issue number4
DOIs
StatePublished - 22 Feb 2001

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