α-diazoacetates as carbene precursors: Metallosalen-catalyzed asymmetric cyclopropanation

Tatsuya Uchida, Tsutomu Katsuki

Research output: Contribution to journalArticle

45 Citations (Scopus)

Abstract

Readily available α-diazo compounds have been shown to be efficient carbene precursors for asymmetric cyclopropanation using ruthenium(NO)-salen and cobalt-salen complexes, as catalysts. The stereoselectivity of the cyclopropanation depends on the metal ion, its valency, the structural and electronic nature of the salen ligand, and the apical ligand of the salen complex used. Both trans- and cis-selective asymmetric intermolecular cyclopropanation can be realized under mild conditions by using a suitable metallosalen complex. Furthermore, a wide range of alkenyl α-diazoacetates and the related alkenyl diazomethyl ketones undergo intramolecular cyclopropanation in a highly enantioselective manner by using various metallosalen complexes, easily prepared in a modular fashion, as catalyst.

Original languageEnglish
Pages (from-to)1715-1723
Number of pages9
JournalSynthesis
Issue number10
DOIs
Publication statusPublished - May 15 2006

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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