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Synlett 1993; 1993(1): 81-82
DOI: 10.1055/s-1993-22357
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Design of New Chiral Auxiliaries for the Stereoselective Nucleophilic Addition to α-Alkoxy Aldehydes: A Remarkable Remote Protecting Group Effect

André B. Charette* , Christophe Mellon, Langis Rouillard, Éric Malenfant
  • *Department of Chemistry, Université de Montréal, Montréal, Canada H3C 3J7
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Publication Date:
19 March 2002 (online)

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The MgBr2·OEt2 mediated addition of allyltributyltin to an α-alkoxyaldehyde bearing a protected 2-hydroxytetrahydropyranyl group was shown to be highly diastereoselective. The sense and the level of induction was shown depend on the nature of the protecting group at C-3.