Enantioselective cyclopropanation reactions with planar-chiral pyridinium ylides: A substituent effect and a remote steric effect

Nobuhiro Kanomata, Ryo Sakaguchi, Kazuki Sekine, Satomi Yamashita, Hiroko Tanaka

研究成果: Article

27 引用 (Scopus)

抜粋

Novel planar-chiral pyridinium ylides were designed, and generated in situ from the corresponding pyridinium salts with triethylamine. Ylides with a common parapyridinophane skeleton reacted efficiently with electron-deficient dicyanoalkenes, or malononitriles, to produce optically active cyclopropane derivatives with high enantioselectivity (up to 99% ee). Remote steric effects were observed on the enantioselectivities, where the R2 groups of the pyridinophane core resulted in higher ee values of the products. Density function theory (DFT) calculations are in good agreement with our experimental results: the energetically favored transition state leads to the major stereoisomer, namely the trans-cyclopropane products.

元の言語English
ページ(範囲)2966-2978
ページ数13
ジャーナルAdvanced Synthesis and Catalysis
352
発行部数17
DOI
出版物ステータスPublished - 2010 11 22

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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