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Catalytic Enantioselective Reactions using Organomanganese Compounds

Organomanganese Compounds (2011)

  1. Nicka Chinkov

Published Online: 15 JUN 2011

DOI: 10.1002/9780470682531.pat0542

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Chinkov, N. 2011. Catalytic Enantioselective Reactions using Organomanganese Compounds. Patai's Chemistry of Functional Groups. .

Author Information

  1. University of Haifa, Faculty of Natural Sciences, Department of Biology and Environment, Oranim, Kiryat Tivon, Israel

Publication History

  1. Published Online: 15 JUN 2011

Abstract

The use of organomanganese reagents in asymmetric catalysis represents an attractive niche for synthetic chemists mainly due to the toxicological benignancy and low cost.

Yet, the arsenal of the existing organomanganese catalysts, processes and substrates used in the enantioselective reactions is quite limited. This chapter covers the chief achievements made within the last quarter of a century in this area. The majority of the transformations are made by the MnIII-salen compounds, which are commonly used as potent oxene- and nitrene-transfer agents in the epoxidation and aziridination reactions of C[DOUBLE BOND]C bonds. The scope, limitations and mechanistic studies of these processes are discussed. Additional class of transformations performed by the MnIII-salen is asymmetric hydroxylation and amination of C[BOND]H bonds as well as formation of S[BOND]O and S[BOND]N in sulfides. Less common Mn-porphyrin and other scarcely studied complexes and their corresponding asymmetric reactions are discussed as well.

Keywords:

  • Chiral manganese(salen);
  • Jacobsen epoxidation;
  • Katsuki epoxidation;
  • asymmetric sulfoxidation;
  • chiral manganese(porphyrin);
  • asymmetric oxidation;
  • asymmetric amidation