Journal
TETRAHEDRON
Volume 62, Issue 40, Pages 9467-9474Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2006.07.051
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The Claisen rearrangement of simple aliphatic allyl vinyl ethers catalyzed by a metalloporphyrin, Cr(TPP)Cl, is described. The porphyrin-based Lewis acid catalyst can effectively accelerate the rearrangement via a concerted [3,3] pathway with a minimal degree of bond ionization of the substrates, providing the corresponding Claisen products in moderate to high yields and almost perfect regioselectivity at low catalyst loading. (c) 2006 Elsevier Ltd. All rights reserved.
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