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Synlett 1996; 1996(8): 745-746
DOI: 10.1055/s-1996-5534
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Unprecedented Electronic and Steric Effects in Palladium-Catalyzed Asymmetric Allylation: Switching of Enantioselectivity with a Single Chiral Backbone

Nobuyoshi Nomura, Yvan C. Mermet-Bouvier, T. V. RajanBabu*
  • *Department of Chemistry, The Ohio State University, 120 W. 18th Ave. Columbus, Ohio 43210, USA
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Publication Date:
31 December 2000 (online)

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In the palladium-catalyzed asymmetric substitution reaction between 1,3-diphenylallyl acetate and sodium salt of diethyl malonate, electron-withdrawing and electron-rich P-substituents in a single chiral back-bone give products of opposite stereochemistry. Sterically bulky substituents have the same effect as electron-rich ones.

asymmetric allylation - palladium catalyst - steric effects - electronic effects - bidentate phosphinites