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Journal
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Synthesis of d-lactones from
2-alkynylepoxides and 4-alkynyl-1,3-dioxolan-2-ones by palladium catalysed carbonylation and conjugate nucleophilic addition.
J.G. Knight, S.W. Ainge, C.A. Baxter, T.P.
Eastman, and S.J. Harwood, J. Chem. Soc., Perkin Trans. 1,
2000,
3188. |
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Abstract: Palladium
catalysed carbonylation of both 4-alkynyl-1,3-dioxolan-2-ones (1)and
alkynylepoxides (2) occurs under mild conditions to give methyl
5-hydroxy-2,3-dienoates (3) which are converted to
g,d-unsaturated
delta-lactones (4) by tandem conjugate addition-cyclisation with
lithium dimethylcuprate or to methyl (E)-5-hydroxypent-3-enoates (5)
by stereoselective reduction with sodium borohydride. |
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