cis- and enantio-selective cyclopropanation with chiral (ON+)Ru-salen complex as a catalyst

Tatsuya Uchida, Ryo Irie, Tsutomu Katsuki

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96 Citations (Scopus)

Abstract

Cyclopropanation of styrene with α-diazoacetate in the presence of (R,R)-(salen)ruthenium complex 4 in THF which dissolves the complex exhibits remarkable cis- and enantio-selectivity [cis:trans=97:3, >97% ee (1S,2R)], while the same reaction in hexane which does not dissolve it shows good but opposite sense of enantioselectivity [-83% ee (1R,2S)] together with moderate cis-selectivity (cis:trans=68:32). In homogeneous and heterogeneous conditions, (salen)ruthenium complexes are considered to have different ligand-conformation which, in turn, causes the opposite sense of enantioface selectivity in the cyclopropanation. 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)3501-3509
Number of pages9
JournalTetrahedron
Volume56
Issue number22
DOIs
Publication statusPublished - May 26 2000

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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