Enantioselective Lewis acid catalysis in intramolecular [2+2] photocycloaddition reactions of coumarins

Hao Guo, Eberhardt Herdtweck, Thorsten Bach

Research output: Contribution to journalArticlepeer-review

126 Scopus citations

Abstract

Photochemistry goes acidic! In the presence of the chiral Lewis acid catalyst 2 the intramolecular [2+2] photocycloaddition of 4-(alk-4- enyl)coumarins (1) provides the corresponding products 3 with up to four stereogenic centers in a highly chemo-(84-89 % yield) and stereoselective fashion. For R=H, enantioselectivities up to 82 % ee are possible with 50 mol % catalyst 2 and up to 78 % ee with only 20 mol % of catalyst 2.

Original languageEnglish
Pages (from-to)7782-7785
Number of pages4
JournalAngewandte Chemie International Edition in English
Volume49
Issue number42
DOIs
StatePublished - 11 Oct 2010

Keywords

  • Chirality
  • Cycloadditions
  • Enantioselectivity
  • Lewis acids
  • Photochemistry

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