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Synthesis of α,α'-trans-oxepanes through an organocatalytic oxa-conjugate addition reaction.
Lanier, Megan L; Kasper, Amanda C; Kim, Hyoungsu; Hong, Jiyong.
Afiliación
  • Lanier ML; Department of Chemistry, Duke University , Durham, North Carolina 27708, United States.
Org Lett ; 16(9): 2406-9, 2014 May 02.
Article en En | MEDLINE | ID: mdl-24724535
ABSTRACT
Oxepanes are found in a wide range of natural products; however, they are challenging synthetic targets due to enthalpic and entropic barriers. Organocatalytic oxa-conjugate addition reactions promoted by the gem-disubstituent (Thorpe-Ingold) effect stereoselectively provided α,α'-trans-oxepanes. In addition, the potential of an organocatalytic tandem oxa-conjugate addition/α-oxidation was demonstrated in a rapid generation of molecular complexity. These organocatalytic oxa-conjugate addition reactions would provide powerful tools for the synthesis of natural products that contain highly functionalized oxepanes.
Asunto(s)

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Oxepinas / Productos Biológicos Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2014 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: EEUU / ESTADOS UNIDOS / ESTADOS UNIDOS DA AMERICA / EUA / UNITED STATES / UNITED STATES OF AMERICA / US / USA

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Oxepinas / Productos Biológicos Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2014 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: EEUU / ESTADOS UNIDOS / ESTADOS UNIDOS DA AMERICA / EUA / UNITED STATES / UNITED STATES OF AMERICA / US / USA