Chiral phosphoric acid catalyzed enantioselective [4 + 2] cycloaddition reaction of α-fluorostyrenes with imines

Research output: Contribution to journalArticlepeer-review

Abstract

An enantioselective [4 + 2] cycloaddition reaction of α-fluorostyrenes with N-benzoyl imines was demonstrated using a chiral phosphoric acid catalyst. Cycloaddition products having fluorine functionality were formed in high yields with excellent diastereo- and enantioselectivities. Further manipulation of the enantioenriched cycloaddition product with silyl enol ether in the presence of BiCl3 catalyst afforded substitution product with retention of the dihydro-4H-1,3-oxazine framework through selective carbon−fluorine bond cleavage without loss of enantiomeric excess.

Original languageEnglish
Pages (from-to)8957-8961
Number of pages5
JournalOrganic letters
Volume22
Issue number22
DOIs
Publication statusPublished - 2020 Nov 20

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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