Download PDF
Synlett 1998; 1998(3): 213-220
DOI: 10.1055/s-1998-1618
account
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Hydrogen and Allylation Transfer Reactions in Acyclic Free Radicals

Yvan Guindon* , Grace Jung, Brigitte Guérin, William W. Ogilvie
  • *Institut de recherches cliniques de Montréal (IRCM), Bio-organic Chemistry Laboratory, 110 des Pins Ouest, Montréal, QC, Canada H2W 1R7; Fax (514) 9 87-57 89; E-mail: guindoy@ircm.umontreal.ca
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Asymmetric induction involving radicals that are flanked by an ester and a stereogenic center bearing a heteroatom has been demonstrated in hydrogen-transfer reactions and allylations. The roles of both structural and electronic features in controlling the facial selectivity of these radical reactions are best rationalized by a transition state model, which resembles the ground state conformation of the radical supported by calculations and ESR studies.

1,2-asymmetric induction - radical reaction - allylation - exocyclic effect - transition state model