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Synlett 1995; 1995(10): 1021-1023
DOI: 10.1055/s-1995-5163
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Control of the Diastereoselectivity of the Allylation and Deuteration of 2-Hydroxyalkyl Aryl Sulfoxides

Philippe Renaud* , Thierry Bourquard
  • *Université de Fribourg, Institut de Chimie Organique, Pérolles, CH-1700 Fribourg, Switzerland
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Publication Date:
31 December 2000 (online)

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Radical allylation and deuteration of diastereomeric 2-hydroxyalkyl aryl sulfoxides were investigated. Modest diastereoselectivities were observed with the syn precursors while the anti ones gave good levels of selectivity. The configuration at C(1) can be inverted by protecting the free OH group as a tert-butyldimethylsilyl ether.

Radical - β-hydroxy sulfoxide - alkylation - diastereoselectivity - 1,2-induction