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Synlett 2001; 2001(5): 0718-0721
DOI: 10.1055/s-2001-13372
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A Four-Step Route from Aldehydes to C2-Elongated Enantiomerically Pure α,β-Unsaturated γ-Hydroxy Esters

Christian Harcken* , Reinhard Brückner
  • *Present address: Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, USA; Fax + 49-761-2 03 61 00; E-mail: reinhard.brueckner@organik.chemie.uni-freiburg.de; charcken@mail.cm.utexas.edu
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Publication Date:
31 December 2001 (online)

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Asymmetric dihydroxylation of β,γ-unsaturated esters 4 provided β-hydroxy-γ-lactones 3 or ent-3. Methanolysis acetonide formation and LDA-mediated fragmentation of the resulting esters 5/ent-5 furnished the γ-chiral acrylates 6/ent-6 containing disubstituted C=C bonds (93-99% ee). Also, β-hydroxy-γ-lactones ent-3 a and 3 b were α-butylated and α-brominated, respectively, prior to methanolysis, acetonide formation, and fragmentation which led to the γ-chiral acrylates 9 and 12 with trisubstituted C=C bonds (94 and 95% ee, respectively).

acetonides - asymmetric dihydroxylation - chiral acrylates - γ-chiral α,β-unsaturated esters - β-hydroxy-γ-lactones