Aluminum triflate catalyzed tandem reactions of d -galactal: Toward chiral benzopyrans, chromenes, and chromans

Sandile B. Simelane, Henok H. Kinfe, Alfred Muller, D. Bradley G. Williams

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

3,4,6-Tri-O-acetyl-d-galactal is selectively converted into 1-O-aryl-2-deoxy derivatives or chiral bridged benzopyrans under Al(OTf)3 catalysis, depending on reaction conditions. The benzopyrans react with Al(OTf)3/acetic anhydride in ring-opening reactions in the absence or presence of acetic acid to selectively produce chiral chromenes or chromans, respectively, in high yields.

Original languageEnglish
Pages (from-to)4543-4545
Number of pages3
JournalOrganic Letters
Volume16
Issue number17
DOIs
Publication statusPublished - 5 Sept 2014

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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