Publikation: Addition of Cerium Reagents Derived from (Trimethylsilyl)propargyl Bromide to Aldehydes
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1994
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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.
Zusammenfassung in einer weiteren Sprache
Fachgebiet (DDC)
540 Chemie
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Cerium Compounds, 1,7-Octadiynes, substituted, Allenes, Stereoids
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ECKENBERG, 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.199419940707BibTex
@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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<dcterms:abstract xml:lang="deu">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.</dcterms:abstract>
<dcterms:bibliographicCitation>First publ. in: Liebigs Annalen der Chemie 1994, 7, pp. 673-677</dcterms:bibliographicCitation>
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