Cyclopropanation with Diazomethane and Bis(oxazoline)palladium(II) Complexes

Scott E. Denmark, Robert A. Stavenger, Anne Marie Faucher, James P. Edwards

Research output: Contribution to journalArticlepeer-review


Studies toward the development of an enantioselective diazomethane-based cyclopropanation reagent derived from bis(oxazoline)palladium(II) complexes are reported. Several simple palladium chelates, 2 and 7, in addition to the novel carbon-bound complexes 15 were synthesized and evaluated in the cyclopropanation of various electron-deficient olefins. The X-ray crystal structure of aryl - bis(oxazoline)palladium complex 15c is described. Although all catalysts efficiently affected cyclopropanation, all products were racemic. An intriguing relationship between substitution on the oxazoline ring, particularly the commonly-derivatized 4-position, and catalyst efficiency was discovered. The results are rationalized by either partial or complete bis(oxazoline) decomplexation during the course of the reaction.

Original languageEnglish (US)
Pages (from-to)3370-3374
Number of pages5
JournalJournal of Organic Chemistry
Issue number10
StatePublished - 1997

ASJC Scopus subject areas

  • Organic Chemistry


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