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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 17, 1987 - Issue 14
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Original Articles

Silafunctional Compounds in Organic Synthesis. XXXVII. Metalated (Allyl) Aminosilanes: Regioselective Coupling with Alkyl Halides to (E)-1-Alkenylsilanes with a Functional Group on Silicon

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Pages 1637-1646 | Published online: 06 Dec 2006

References

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  • Colvin , E. 1981 . “Silicon in Organic Synthesis,” , London : Butterworths . Weber, W. P., “Silicon Reagents for Organic Synthesis,” Springer-Verlag, Berlin, 1983
  • Lukevics , E. , Belyakova , Z. V. , Pomerantseva , M. G. and Voronkov , M. G. 1977 . J. Organomet. Chem. Libr. , 5 : 1
  • Tamao , K. , Akita , M. , Maeda , K. and Kumada , M. 1987 . J. Org. Chem. , 52 : 1100 E. g. (footnote No. 20)
  • Tamao , K. 1985 . “Organosilicon and Bioorganosilicon Chemistry,” , Edited by: Sakurai , H. 231 – 242 . Chichester : Ellis Horwood .
  • Koumaglo , K. and Chan , T. H. 1984 . Tetrahedron Lett. , 25 : 717 Chan, T. H. and Koumaglo, K., J. Organomet. Chem., 1985, 285, 109
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  • Muchowski , J. M. , Naef , R. and Maddox , M. L. 1985 . Tetrahedron Lett. , 26 : 5375
  • A similar coupling of a potassium reagent derived from allyl(t-butoxy)dimethylsilane, however, gave the α product predominantly, γ/α = 1/2.6. The result suggests that an electronic effect by the functional group on silicon is also an important factor for the regiocontrol

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