Efficient one-step synthesis of chiral bidentate oxazoline-alcohol ligands via a cyclic imidate ester rearrangement

Noël, Timothy;Robeyns, Koen;Van Meervelt, Luc;Van der Eycken, Erik;Van der Eycken, Johan
(2009) Tetrahedron: Asymmetry — Vol. 20, n° 17, p. 1962-1968 (2009)

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Authors
  • Noël, Timothy
    Author
  • Robeyns, KoenUCLouvain
    Author
  • Van Meervelt, Luc
    Author
  • Van der Eycken, Erik
    Author
  • Van der Eycken, Johan
    Author
Abstract
Various chiral bidentate oxazoline-alcohol ligands were obtained in a straightforward one-step synthesis via a cyclic imidate ester rearrangement. These chiral ligands were tested and compared in asymmetric diethylzinc additions to aldehydes resulting in selectivities of up to 87% ee. An interesting chirality switch was observed when a CPh2-tether instead of a CH2 was present, offering the opportunity for dual stereocontrol. © 2009 Elsevier Ltd. All rights reserved.
Affiliations
  • KU LEUVENDepartment of Chemistry

Citations

Noël, T., Robeyns, K., Van Meervelt, L., Van der Eycken, E., & Van der Eycken, J. (2009). Efficient one-step synthesis of chiral bidentate oxazoline-alcohol ligands via a cyclic imidate ester rearrangement. Tetrahedron: Asymmetry, 20(17), 1962-1968. https://doi.org/10.1016/j.tetasy.2009.07.038 (Original work published 2009)