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Synlett 1997; 1997(1): 41-43
DOI: 10.1055/s-1997-709
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Pinacol Cross Coupling Reactions of Ethyl 2-Alkyl-2-Formylpropionates. Stereoselective Synthesis of 2,2,4-Trialkyl-3-Hydroxy-γ-Butyrolactones

Min Kang, Jeonghan Park, Steven F. Pedersen*
  • *Department of Chemistry, University of California, Berkeley, CA 94706, E-mail: pedersen@cchem.berkeley.edu
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Publication Date:
22 March 2004 (online)

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Intermolecular pinacol coupling of ethyl 2-alkyl-2-formylpropionates (2) (i.e. EtOC(O)CR1MeCHO) with non-chelating aldehydes provides high yields of threo diols. The reaction is promoted by vanadium(II) ions which are conveniently generated in situ from VCl3(THF)3 and zinc dust. high diastereofacial selectivity is observed when starting with chiral 2, or chiral non-chelating aldehydes.

Pinacol coupling - vanadium - lactone - diol