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Synlett 1999; 1999(11): 1793-1795
DOI: 10.1055/s-1999-2955
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Highly cis- and Enantioface-Selective Cyclopropanation Using (R,R)-Ru-Salen Complex: Solubility Dependent Enantioface Selection

Tatsuya Uchida* , Ryo Irie, Tsutomu Katsuki
  • *Department of Molecular Chemistry, Graduate School of Science, Kyushu University 33, Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan; Fax +81 92 6 42 26 07
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Publication Date:
31 December 1999 (online)

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The reaction of styrene and t-butyl α-diazoacetate in the presence of (R,R)-(ON+)(salen)ruthenium(II) complex 1 under the irradiation of incandescent light in THF gave the corresponding (1S,2R)-cyclopropanecarboxylate with high stereoselectivity of 99% ee (cis : trans = 96 : 4), while the same reaction in hexane gave the enantiomeric (1R,2S)-cyclopropanecarboxylate preferentially (83% ee, cis : trans = 68 : 32).

(ON+)(salen)ruthenium(II) complex - photo-activation - cyclopropanation - cis-selectivity

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