Reinvestigation of a Catalytic, Enantioselective Alkene Dibromination and Chlorohydroxylation

Scott E. Denmark, Nessa Carson

Research output: Contribution to journalArticlepeer-review

Abstract

Attempts to reproduce eight, putative, enantioselective dibromination and chlorohydroxylation reactions from oft-cited literature studies are described. The reactions were performed with full fidelity to the original report wherever possible. Analysis of the enantiomeric composition was performed by chiral stationary phase HPLC or SFC (CSP-HPLC or CSP-SFC), as opposed to the original report, which used chiral shift reagent NMR spectroscopy. After careful study, the reported levels of enantioselectivity were found to be incorrect. Possible explanations for the false positive results are discussed.

Original languageEnglish (US)
Pages (from-to)5728-5731
Number of pages4
JournalOrganic Letters
Volume17
Issue number23
DOIs
StatePublished - Nov 13 2015

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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