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Synthesis 1996; 1996(5): 586-588
DOI: 10.1055/s-1996-4266
short paper
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Stereoselective Synthesis of Methyl (Z)-3-Iodo-2-(1-hydroxyalkyl)prop-2-enoates and Their Further Transformation to α-(Z)-Iodomethylene-β-lactones

Chunming Zhang, Xiyan Lu*
  • *Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China, Fax +86(21)64166128
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Publication Date:
31 December 2000 (online)

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The tandem nucleophilic addition-aldol reaction of methyl propynoate, iodide ion, and aldehydes or ketones in the presence of ZrCl4 as the catalyst gave methyl 3-iodo-2-(1-hydroxyalkyl)prop-2-enoates with high Z selectivity, which were further transformed to α-(Z)-iodomethylene-β-lactones in good yield.

propynoate - tandem nucleophilic addition-aldol reaction - Z selectivity - (Z)-3-iodo-2-(1-hydroxyalkyl)prop-2-enoates - α-(Z)-iodomethylene-β-lactones