Asymmetric transfer hydrogenation of α,β-unsaturated, α-tosyloxy and α-substituted ketones

Asymmetric transfer hydrogenation of cyclic and acyclic α,β-unsaturated ketones catalysed by η 6- p-cymene/ruthenium(II) and η 5-pentamethylcyclopentadienyl/rhodium(III) complexes have been investigated. Cyclic α,β-unsaturated ketones appeared to be more suitable substrates for the synthesis of enan...

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Bibliographic Details
Published in:Tetrahedron 2006-02, Vol.62 (8), p.1864-1876
Main Authors: Peach, Philip, Cross, David J., Kenny, Jennifer A., Mann, Inderjit, Houson, Ian, Campbell, Lynne, Walsgrove, Tim, Wills, Martin
Format: Article
Language:English
Subjects:
Asymmetric
Hydrogenation
Ketone
Reduction
Ruthenium
Transfer
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Summary:Asymmetric transfer hydrogenation of cyclic and acyclic α,β-unsaturated ketones catalysed by η 6- p-cymene/ruthenium(II) and η 5-pentamethylcyclopentadienyl/rhodium(III) complexes have been investigated. Cyclic α,β-unsaturated ketones appeared to be more suitable substrates for the synthesis of enantiomerically pure allylic alcohols than do acyclic α,β-unsaturated ketones. A proposed mechanism for the formation of 4-phenyl-[1,3]-dioxolan-2-one from α-tosyloxy- and halo-substituted acetophenones is discussed. The results of further investigations into the reduction of a range of α-tosyloxyacetophenones and the dynamic kinetic resolution of α-substituted ketones is presented. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.11.036