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Synlett 1994; 1994(1): 1-26
DOI: 10.1055/s-1994-22728
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Acyclic Diastereofacial Selection in Intermolecular Radical Reactions Steric vs Electronic Controls

William SMADJA*
  • *Laboratoire de Chimie Organique associé au CNRS, Université Pierre et Marie Curie; Case 181 ; 4, Place Jussieu 75252 Paris Cedex 05, FRANCE
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Publication Date:
22 March 2002 (online)

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Starting from chiral acyclic substrates, stereoselective intermolecular radical reactions leading to 1,2 and 1,4-asymmetric inductions are described. The synthetic usefulness of these reactions occuring through radical processes being demonstrated, a rationalization of the 1,2-asymmetric induction is attempted in terms of steric vs electronic controls . 1 Introduction 2 Relative 1,2-Asymmetric Inductions (Substrate Control). 2.1 α-Chiral Radicals A (Tables I to IV). 2.2 α-Chiral Olefins B ((Table V). 3 Relative 1,4-Asymmetric Inductions (Chiral Auxiliary Control) 3.1 δ-Chiral Radicals C (Table VI) 3.2 δ-Chiral Olefins D) (Table VII) 4 Conclusion