Enthalpy- and/or entropy-controlled asymmetric oxidation: Stereocontrolling factors in Mn-salen-catalyzed oxidation

T. Nishida, A. Miyafuji, Y. N. Ito, T. Katsuki

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Abstract

The degree of enantioselection by second-generation Mn-salen complexes was found to depend upon the conformation of their ligand and substrate nucleophilicity. Oxidation of usual olefins was better effected by using (R,S)-Mn-salen complexes as catalysts, while that of more nucleophilic ones was achieved by using (R,R)-Mn-salen complexes. This phenomenon was explained by analyzing the enthalpy and entropy factors of the reactions. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)7053-7058
Number of pages6
JournalTetrahedron Letters
Volume41
Issue number36
DOIs
Publication statusPublished - Sep 2 2000

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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