Addition of Cerium Reagents Derived from (Trimethylsilyl)propargyl Bromide to Aldehydes

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1994
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Eckenberg, Peter
Köhler, Thomas
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Liebigs Annalen der Chemie. 1994, 1994(7), pp. 673-677. ISSN 0170-2041. eISSN 1099-0690. Available under: doi: 10.1002/jlac.199419940707
Zusammenfassung

The addition of (trimethylsilyl)propargylmagnesium bromide (9) to aldehydes afforded predominantly the allenylic alcohols rac-10. The regioselectivity of this addition changes dramatically when organocerium reagents were used for the addition. In this case nearly exclusive formation of the homopropargylic alcohols rac-8 was observed. Highest selectivity for this process was obtained when cerium(III) isopropoxide (13) was used as a precursor for the formation of the organocerium reagent.

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540 Chemie
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Cerium Compounds, 1,7-Octadiynes, substituted, Allenes, Stereoids
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ISO 690ECKENBERG, Peter, Ulrich GROTH, Thomas KÖHLER, 1994. Addition of Cerium Reagents Derived from (Trimethylsilyl)propargyl Bromide to Aldehydes. In: Liebigs Annalen der Chemie. 1994, 1994(7), pp. 673-677. ISSN 0170-2041. eISSN 1099-0690. Available under: doi: 10.1002/jlac.199419940707
BibTex
@article{Eckenberg1994Addit-9844,
  year={1994},
  doi={10.1002/jlac.199419940707},
  title={Addition of Cerium Reagents Derived from (Trimethylsilyl)propargyl Bromide to Aldehydes},
  number={7},
  volume={1994},
  issn={0170-2041},
  journal={Liebigs Annalen der Chemie},
  pages={673--677},
  author={Eckenberg, Peter and Groth, Ulrich and Köhler, Thomas}
}
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