en
Scientific article
Letter
English

Copper-catalyzed desymmetrization of n-sulfonylaziridines with methylmagnesium halides

Published inOrganic letters, vol. 1, no. 3, p. 439-441
Publication date1999-06-25
First online date1999-06-25
Abstract

Cyclohexene N-p-toluenesulfonylimine (1) undergoes enantioselective ring opening to 2b upon treatment with methylmagnesium halides or MeLi in the presence of chiral Cu-catalysts. No activation of the aziridine by Lewis acid is required. Enantioselectivities of up to 91% have been observed under optimized conditions with the chiral imine ligand derived from phenylalanine. The same system reacts with cyclohexene oxide to afford trans-2-methylcyclohexanol with 50% yield and 10% ee.

eng
Keywords
  • Aziridines
  • Catalysts
  • Ethers
  • Reagents
  • Stereoselectivity
Citation (ISO format)
MÜLLER, Paul, NURY, Patrice. Copper-catalyzed desymmetrization of <i>n</i>-sulfonylaziridines with methylmagnesium halides. In: Organic letters, 1999, vol. 1, n° 3, p. 439–441. doi: 10.1021/ol990650b
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Article (Published version)
accessLevelRestricted
Identifiers
ISSN of the journal1523-7052
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