Journal
TETRAHEDRON
Volume 64, Issue 29, Pages 6863-6869Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.04.056
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Palladium (II)-catalyzed [3,3] sigmatropic rearrangement of acyclic allyl vinyl ethers delivers 2,3-anti disubstituted pentenal Claisen adducts with high diastereoselectivity. Reaction conditions for circumventing allyl vinyl ether cleavage that had previously plagued catalyzed rearrangement of alpha-unsubstituted vinyl ether substrates are described. Merging Pd(II) catalysis with the facile access to the Claisen substrates afforded by Ir(I)-catalyzed olefin isomerization provides an expedient procedure for realizing asymmetric anti-selective Claisen rearrangements. (C) 2008 Elsevier Ltd. All Fights reserved.
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