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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 27, 1997 - Issue 6
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Original Articles

Chelation-Controlled Regioselection in Palladium-Catalyzed Carbonyl Allylation by 4-Pentene-1,3-Diol or Its Cyclic Carbonate

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Pages 1015-1021 | Received 30 Jul 1996, Published online: 22 Aug 2006

References

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  • Takahara , J. P. , Masuyama , Y. and Kurusu , Y. 1992 . J. Am. Chem. Soc. , 114 : 2577 Masuyama, Y. in “Advances in Metal-Organic Chemistry,” Liebeskind, L. S. Ed, JAI Press, London, 1994, Vol. 3, pp. 255–303
  • Bando , T. , Tanaka , S. , Fugami , K. , Yoshida , Z. and Tamaru , Y. 1992 . Bull. Chem. Soc. Jpn. , 65 : 97
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  • The coupling constant (J 112,113=0 Hz) between 2-H and 3-H in 1H NMR (JEOL GX-270) of 2-phenyl-3-vinyltetrahydrofuran (5; R=Ph) suggested that the stereochemistry in a major isomer of all 2-substituted 3-vinyltetrahydrofurans 5 was trans (cis:trans=1:9).
  • Cyclic carbonate of 4-hexene-1,3-diol, namely 4-[(E)-2-propenyl]-1,3-dioxan-2-one caused the carbonyl allylation at room temperature neither in DMF nor in THF.

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