Determining the Relative Configuration of Propargyl Cyclopropanes by Co-Crystallization

Research output: Contribution to journalResearch articleContributedpeer-review


  • Felix Krupp - , University of Stuttgart (Author)
  • Marie Idrissa Picher - , University of Stuttgart (Author)
  • Wolfgang Frey - , University of Stuttgart (Author)
  • Bernd Plietker - , Chair of Organic Chemistry I, Technische Universität Dresden (Author)
  • Clemens Richert - , University of Stuttgart (Author)


Determining the diastereoselectivity of new synthetic mo­lecules can be a challenge when NMR methods fail and the compounds are difficult to crystallize. Encapsulating organic crystals can be used to overcome this challenge. Here we show that the diastereomeric confi­guration of racemic mixtures of propargyl cyclopropanes can be determined by co-crystallization with 1,3,5,7-tetrakis(2-bromo-4-methoxyphenyl)adamantane and X-ray crystallography. Three crystal structures are reported that unambiguously identify the products of Fe-catalyzed cyclopropanations as cis - or trans -isomers. These findings expand the scope of co-crystallization with tetraaryladamantanes as a method to determine the stereochemical configuration of organic molecules that are difficult to crystallize by themselves.


Original languageEnglish
Pages (from-to)350-353
Issue number4
Publication statusAccepted/In press - 2020


ASJC Scopus subject areas


  • crystallization, diastereomers, stereochemistry, structure elucidation, X-ray crystallography

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