Remote steric effects of C2-symmetric planar-chiral terpyridine ligands on copper-catalyzed asymmetric cyclopropanation reactions

Nanako Mugishima, Nobuhiro Kanomata, Norihiko Akutsu, Hironobu Kubota

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

A series of enantioselective cyclopropanation reactions of substituted alkenes with diazoacetates was investigated in the presence of Cu(OTf)2 with C2-symmetric planar-chiral bridged 2,2′:6′,2″-terpyridines. Planar-chiral terpyridine-copper complexes exhibited moderate diastereomeric excesses with good enantioselectivities of cis-cyclopropane products in catalytic asymmetric cyclopropanation reactions of various styrene derivatives with ethyl diazoacetate. A remote steric effect was found to enhance enantioselectivity for the cyclopropanation induced by a sterically demanding substituent beyond the ansa-bridge of pyridinophane ligands on the other side of the reaction site as a relay of steric influences through flexible cyclophane bridges.

Original languageEnglish
Pages (from-to)1898-1903
Number of pages6
JournalTetrahedron Letters
Volume56
Issue number14
DOIs
Publication statusPublished - 2015 Apr 1

Keywords

  • Asymmetric cyclopropanation
  • Copper carbenoid
  • Planar chirality
  • Remote steric effect
  • Terpyridine

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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