Hydrogen and Allylation Transfer Reactions in Acyclic Free Radicals

Yvan Guindon; Grace Jung; Brigitte Guérin; William W. Ogilvie

doi:10.1055/s-1998-1618

Synlett 1998; 1998(3): 213-220
DOI: 10.1055/s-1998-1618

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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

Abstract

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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

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