Journal
TETRAHEDRON
Volume 62, Issue 5, Pages 1025-1032Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.09.148
Keywords
configuration; Diels-Alder reactions; heterogeneous catalysis; hydrogen bonding; Lewis acids
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Chiral bis(oxazoline) complexes of Cu(II), Zn(II) and Mg(II) have been immobilized on silica support via hydrogen-bonding interactions. Up to 93% ee is obtained in the Diels-Alder reaction between 3-((E)-2-butenoyl)-1,3-oxazolin-2-one and cyclopentadiene at room temperature with the heterogeneous bis(oxazoline) complexes, and the catalysts can be recycled without losing enantioselectivity. Experimental and theoretical studies show that the reversal of the absolute product configuration upon immobilization of the PhBOX-Cu(II) catalyst is triggered by the anion dissociation from Cu(II) onto the surface of the support. (c) 2005 Elsevier Ltd. All rights reserved.
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