Steric control of α- and β-alkylation of azulenone intermediates in a guanacastepene A synthesis

  1. Wang, H. 2
  2. Michalak, K. 3
  3. Michalak, M. 3
  4. Jiménez-Osés, G. 1
  5. Wicha, J. 3
  6. Houk, K.N. 2
  1. 1 Universidad de Zaragoza
    info

    Universidad de Zaragoza

    Zaragoza, España

    ROR https://ror.org/012a91z28

  2. 2 University of California Los Angeles
    info

    University of California Los Angeles

    Los Ángeles, Estados Unidos

    ROR https://ror.org/046rm7j60

  3. 3 Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warsaw 42, Poland
Mostrar afiliaciones +
Revista:
Journal of Organic Chemistry

ISSN: 0022-3263

Año de publicación: 2010

Volumen: 75

Número: 3

Páginas: 762-766

Tipo: Artículo

DOI: 10.1021/JO902283A PMID: 20039618 SCOPUS: 2-s2.0-75749112537 WoS: WOS:000273982900027 GOOGLE SCHOLAR

Otras publicaciones en: Journal of Organic Chemistry

Resumen

(Chemical Equation Presented) The origins of different stereoselectivities observed experimentally in the alkylations of azulenone precursors in the guanacastepene A synthesis have been determined through density functional theory investigations. The optimized transition structures of methylation of two different guanacastepene A precursors show that steric effects, rather than torsional factors that often determine such stereoselectivities, dictate the preferred products observed. ©2009 American Chemical Society.