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

Takashi Sawada, Masahisa Nakada

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

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
Volume347
Issue number11-13
DOIs
Publication statusPublished - 2005 Oct 1

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Asymmetric catalysis of intramolecular cyclopropanation of 5-aryl-1-diazo-1-mesitylsulfonyl-5-hexen-2-ones'. Together they form a unique fingerprint.

  • Cite this