Catalytic enantioselective cyclopropanation with bis(halomethyl)zinc reagents. II. The effect of promoter structure on selectivity

Scott E. Denmark, Beritte L. Christenson, Stephen P. O'Connor

Research output: Contribution to journalArticle

Abstract

The catalytic, enantioselective cyclopropanation of cinnamyl alcohol has been accomplished with bis(iodomethyl)zinc in the presence of chiral bis(sulfonamides) derived from cyclohexanediamine. An extensive survey of diamine and sulfonamide structure has revealed a marked sensitivity to the spatial relationship of the amine groups, but only a modest dependence on the sulfonamide residue.

Original languageEnglish (US)
Pages (from-to)2219-2222
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number13
DOIs
StatePublished - Mar 27 1995

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Keywords

  • Cyclopropanation
  • allylic alcohol
  • bis(iodomethyl)zinc
  • chiral diamines

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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