Reactivity versus Stability of Oxiranes under Palladium-Catalyzed Reductive Conditions

This review highlights the different selectivities and efficiencies of the Pd‐catalyzed reductive procedures that have been applied to substrates containing an epoxide ring. The proposed mechanisms are also described with, in some cases, personal comments. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2009-03, Vol.2009 (7), p.961-985
Main Authors: Thiery, Emilie, Le Bras, Jean, Muzart, Jacques
Format: Article
Language:English
Subjects:
Alcohols
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemical reactivity
Chemistry
Cleavage reactions
Epoxides
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Heterogeneous catalysis
Homogeneous catalysis
Hydrogenolysis
Kinetics and mechanisms
Organic chemistry
Oxygen heterocycles
Palladium
Preparations and properties
Reactivity and mechanisms
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Summary:This review highlights the different selectivities and efficiencies of the Pd‐catalyzed reductive procedures that have been applied to substrates containing an epoxide ring. The proposed mechanisms are also described with, in some cases, personal comments. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) The palladium‐catalyzed hydrogenolyses of epoxides are reviewed according to the structure of the substrates and reducing agents. The regio‐, stereo‐, and chemoselectivities of the reactions are discussed, as are the mechanisms.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200800739