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

Nanako Mugishima, Nobuhiro Kanomata, Norihiko Akutsu, Hironobu Kubota

研究成果: Article査読

6 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)1898-1903
ページ数6
ジャーナルTetrahedron Letters
56
14
DOI
出版ステータスPublished - 2015 4 1

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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