Catalytic asymmetric intramolecular cyclopropanation of 2-diazo-3-oxo-6-heptenoic acid esters

Hiroyuki Takeda, Masahiro Honma, Ryoji Ida, Takashi Sawada, Masahisa Nakada

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

This manuscript describes studies on the catalytic asymmetric intramolecular cyclopropanation (IMCP) of 2-diazo-3-oxo-6-heptenoic acid esters. The enantioselectivity depends on the bulkiness of the ester moiety, and the 2,6-di-tert-butyl-4-methylphenyl ester of 2-diazo-3-oxo-6-heptenoic acid provided the product with 78% ee, suggesting that the catalytic asymmetric IMCP of α-diazo-β-keto esters could be a key reaction for the enantioselective synthesis of natural products as well as artificial molecules.

Original languageEnglish
Pages (from-to)579-582
Number of pages4
JournalSynlett
Issue number4
DOIs
Publication statusPublished - 2007 Mar 1

Keywords

  • Asymmetric catalysis
  • Cyclopropanation
  • Enantioselectivity
  • Intramolecular reaction
  • α-diazo-β-keto ester

ASJC Scopus subject areas

  • Organic Chemistry

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