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Synlett 1999; 1999(9): 1462-1464
DOI: 10.1055/s-1999-2836
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First Example of Chelation Control during Radical Cascade Reactions of β-Hydroxyester Derivatives

Philippe Renaud* , Laura Andrau, Kurt Schenk
  • *Université de Fribourg, Institut de Chimie Organique, Pérolles, CH-1700 Fribourg, Switzerland
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Publication Date:
31 December 1999 (online)

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The stereoselectivity of radical cyclizations and cascade reactions starting from β-hydroxyester derivatives is efficiently controlled by conversion of the free β-hydroxy group into aluminum alkoxides. Under these conditions, efficient chelation control is occurring. Remarkably, this approach gave also excellent results with acid sensitive radical precursors such as vinylcyclopropanes.

radical reactions - Lewis acids - aluminum - chelates - stereoselectivity - domino reactions