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Synlett 1990; 1990(10): 613-614
DOI: 10.1055/s-1990-21185
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Stereoselective Conjugate Addition of Organolithium Reagents to Enoates Derived from Glyceraldehyde Acetonide

John Leonard* , Gary Ryan, Philip A. Swain
  • *Department of Chemistry, University of Salford, Salford, M5 4WT, England
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Publication Date:
08 March 2002 (online)

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Alkyllithium reagents react preferentially 1,4 and in a highly syn stereoselective manner with γ-alkoxy enoates (alkyl 4,5-isopropylidenedioxy-2-pentenoates) derived from glyceraldehyde acetonide (2,3-isopropylidenedioxy-1-propanal), to provide synthetically useful chiral building blocks. We suggest a transition-state model for such additions based on MM2 calculations.

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