Stereoselective functionalization of cyclopropane derivatives using bromine/magnesium and sulfoxide/magnesium exchange reactions

Felix Kopp, Genia Sklute, Kurt Polborn, Ilan Marek, Paul Knochel

Research output: Contribution to journalArticle

31 Scopus citations

Abstract

(Chemical Equation Presented) The reaction of 2,2-dibromo-1-methyl- cyclopropanecarbonitrile (1) with i-PrMgCl in Et2O/CH 2Cl2 provides the cis-magnesium-carbenoid (2), which reacts with high retention of configuration with various electrophiles. If E = SPh, a stereoselective generation of a quaternary center via a sequential Br/Mg- and sulfoxide/Mg-exchange can be achieved.

Original languageEnglish (US)
Pages (from-to)3789-3791
Number of pages3
JournalOrganic Letters
Volume7
Issue number17
DOIs
StatePublished - Aug 18 2005

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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