Surface confinement effects on enantioselective cyclopropanation. Reactions with supported chiral 8-oxazolinylquinoline-copper complexes

  1. Fraile, J.M. 1
  2. García, J.I. 1
  3. Jiménez-Osés, G. 1
  4. Mayoral, J.A. 1
  5. Roldán, M. 1
  1. 1 Instituto de Nanociencia y Materiales de Aragón
    info

    Instituto de Nanociencia y Materiales de Aragón

    Zaragoza, España

    ROR https://ror.org/031n2c920

Revista:
Organometallics

ISSN: 0276-7333

Año de publicación: 2008

Volumen: 27

Número: 10

Páginas: 2246-2251

Tipo: Artículo

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DOI: 10.1021/OM7010408 SCOPUS: 2-s2.0-44649193969 WoS: WOS:000255768900017 GOOGLE SCHOLAR

Otras publicaciones en: Organometallics

Resumen

Chiral quinolinoxazoline ligands, a class of C1-symmetric chiral ligands, are tested in the enantioselective supported catalysis of a cyclopropanation reaction, trying to improve surface confinement effects of the clay support on the reaction stereoselectivity. In the case of trans/cis diastereoselectivity, these surface effects lead to a complete reversal of selectivity, with cis selectivity values superior to those previously found using C2-symmetryic bisoxazoline ligands. On the other hand, the enantioselectivities do not display important variations in the supported catalysts. A theoretical (DFT) mechanistic study is carried out to explain the origin of the enantioselectivity in homogeneous phase at a molecular level. © 2008 American Chemical Society.