Forming tertiary organolithiums and organocuprates from nitrile precursors and their bimolecular reactions with carbon electrophiles to form quaternary carbon stereocenters

  1. Schnermann, M.J. 1
  2. Untiedt, N.L. 1
  3. Jiménez-Osés, G. 2
  4. Houk, K.N. 2
  5. Overman, L.E. 1
  1. 1 University of California, Irvine
    info

    University of California, Irvine

    Irvine, Estados Unidos

    ROR https://ror.org/04gyf1771

  2. 2 University of California Los Angeles
    info

    University of California Los Angeles

    Los Ángeles, Estados Unidos

    ROR https://ror.org/046rm7j60

Revista:
Angewandte Chemie International

ISSN: 1433-7851

Año de publicación: 2012

Volumen: 51

Número: 38

Páginas: 9581-9586

Tipo: Artículo

DOI: 10.1002/ANIE.201205001 PMID: 22927041 SCOPUS: 2-s2.0-84866434544 WoS: WOS:000308713300020 GOOGLE SCHOLAR

Otras publicaciones en: Angewandte Chemie International

Resumen

Unstabilized tertiary organolithium intermediates are conveniently generated by reductive decyanation of nitriles, and these reagents and their derived cuprates couple in useful yields with carbon- centered electrophiles (see example). Chiral tertiary organolithium and organocuprate derivatives of substituted cis-perhydroazulenes and cis-perhydropentalenes react with electrophiles with high diastereoselectivity from the more-hindered concave face. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.