Asymmetric catalysis of intramolecular cyclopropanation of 5-aryl-1-diazo-1-mesitylsulfonyl-5-hexen-2-ones

Takashi Sawada, Masahisa Nakada*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

47 Citations (Scopus)


We have examined the catalytic asymmetric intramolecular cyclopropanation (IMCP) reactions of 5-aryl-1-diazo-1-mesitylsulfonyl-5-hexen-2-ones, and found that the substituent of the 5-aryl group dramatically changes the enantioselectivity. That is, no enantioselectivity was observed when the substituent was a methoxy group; however, enantioselectivity was moderate when the substituent was a methylenedioxy group or a tert-butyldimethylsilyloxy group, and it dramatically increased when the substituent was lacking (96% ee) or a benzoyloxy group (93% ee).

Original languageEnglish
Pages (from-to)1527-1532
Number of pages6
JournalAdvanced Synthesis and Catalysis
Issue number11-13
Publication statusPublished - 2005 Oct 1


  • Asymmetric catalysis
  • Cyclization
  • Cyclopropanes
  • Diazo compounds
  • Enantioselectivity

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry


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