The first reagent-controlled asymmetric halolactonizations. Dihydroquinidine-halogen complexes as chiral sources of positive halogen ion

Robert B. Grossman, Robert J. Trupp

Research output: Contribution to journalArticlepeer-review

75 Scopus citations

Abstract

The first reagent-controlled asymmetric halolactonizations are described. Complexes of I+ with O-acyl- and O-aryldihydroquinidines are used to promote the asymmetric halolactonization of prochiral Γ,δ-unsaturated carboxylic acids with low but measurable and reproducible enantioselectivity. Experimental factors affecting the ee's are described.

Original languageEnglish
Pages (from-to)1233-1237
Number of pages5
JournalCanadian Journal of Chemistry
Volume76
Issue number9
DOIs
StatePublished - 1998

Keywords

  • Chiral
  • Halocyclization
  • Halogenation
  • Halonium ions
  • Stereoselective

ASJC Scopus subject areas

  • Catalysis
  • Chemistry (all)
  • Organic Chemistry

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