Journal
JOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume 689, Issue 2, Pages 380-386Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2003.10.026
Keywords
chiral palladium complexes; ylide complexes; phosphoniophosphines; chiral sulfoxides; allylic substitution
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A new type of phosphino-phosphonium ylide ligand bearing a chiral sulfinyl center affords a P,C-chelated palladium(II) complex with a resolved asymmetric ylidic carbon atom. According to P-31 NMR analysis of the crude material, the diastereoselectivity of the complexation at room temperature is ca. 7:1. In the crystal state, an X-ray diffraction analysis of one epimer reveals a quasi C-2-symmetric chloro-bridged dinuclear structure, where the (S) configuration of the sulfur atom induces a (S) configuration of the ylidic carbon atom. A in situ Pd(0) catalyst generated from the phosphino-ylide and Pd(PPh3)(4) promotes allylic substitution of 3-acetoxy-1,3-diphenylpropene by sodium malonate in 70% yield and 5% e.e. (C) 2003 Elsevier B.V. All rights reserved.
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