4.4 Article

Asymmetric Friedel-Crafts alkylation of activated benzenes with methyl (E)-2-oxo-4-aryl-3-butenoates catalyzed by [Pybox/Sc(OTf)3]

Journal

TETRAHEDRON
Volume 66, Issue 16, Pages 3024-3029

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.02.054

Keywords

Asymmetric catalysis; Friedel-Crafts reaction; Enantioselectivity; PYBOX ligand; Scandium triflate

Funding

  1. Ministero dell'Universita e della Ricerca (MUR)
  2. University of Pavia

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The asymmetric Friedel-Crafts reaction between methyl (E)-2-oxo-4-aryl-3-butenoates (la-c) and activated benzenes (2a-d) has been efficiently catalyzed by the Sc-III triflate complex of (4'S,5'S)-2,6-bis[4'-(triisopropylsilyl) oxymethyl-5'-phenyl-1',3'-oxazolin-2'-yl]pyridine (pybox 3). The 4,4-diaryl-2-oxo-butyric acid methyl esters (4) are usually formed in good yields and the enantioselectivity is up to 99% ee. The sense of the stereoinduction can be rationalized with the same octahedral complex (10) between 1, pybox 3 and Sc triflate already proposed for other reactions involving pyruvates, and catalyzed by the same complex. (C) 2010 Elsevier Ltd. All rights reserved.

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