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Asymmetric transfer hydrogenation of alpha,beta-unsaturated, alpha-tosyloxy and alpha-substituted ketones
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UNSPECIFIED (2006) Asymmetric transfer hydrogenation of alpha,beta-unsaturated, alpha-tosyloxy and alpha-substituted ketones. TETRAHEDRON, 62 (8). pp. 1864-1876. doi:10.1016/j.tet.2005.11.036 ISSN 0040-4020.
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Official URL: http://dx.doi.org/10.1016/j.tet.2005.11.036
Abstract
Asymmetric transfer hydrogenation of cyclic and acyclic alpha,beta-unsaturated ketones catalysed by eta(6)-p-cymene/ruthenium(II) and eta(5)-pentamethylcyclopentadienyl/rhodium(III) complexes have been investigated. Cyclic or alpha,beta-unsaturated ketones appeared to be more Suitable substrates for the synthesis of enantiomerically pure allylic alcohols than do acyclic alpha,beta-unsaturated ketones. A proposed mechanism for the formation of 4-phenyl-[1,3]-dioxolan-2-one from alpha-tosyloxy- and halo-substituted acetophenones is discussed. The results of further investigations into the reduction of a range of alpha-tosyloxyacetophenones and the dynamic kinetic resolution of alpha-substituted ketones is presented. (c) 2005 Elsevier Ltd. All rights reserved.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Journal or Publication Title: | TETRAHEDRON | ||||
Publisher: | PERGAMON-ELSEVIER SCIENCE LTD | ||||
ISSN: | 0040-4020 | ||||
Official Date: | 20 February 2006 | ||||
Dates: |
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Volume: | 62 | ||||
Number: | 8 | ||||
Number of Pages: | 13 | ||||
Page Range: | pp. 1864-1876 | ||||
DOI: | 10.1016/j.tet.2005.11.036 | ||||
Publication Status: | Published |
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