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

Eckenberg, Peter; Groth, Ulrich; Köhler, Thomas

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

Files

Addition_of_Cerium_Reagents_Derived_from.pdf(618.23 KB)

Date

1994

Authors

Eckenberg, Peter

Groth, Ulrich

Köhler, Thomas

Publication type

Journal article

Published in

Liebigs Annalen der Chemie ; 1994 (1994), 7. - pp. 673-677. - ISSN 0170-2041. - eISSN 1099-0690

Abstract

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.

Subject (DDC)

540 Chemistry

Keywords

Cerium Compounds,1,7-Octadiynes,substituted,Allenes,Stereoids

Cite This

ISO 690

ECKENBERG, Peter, Ulrich GROTH, Thomas KÖHLER, 1994. Addition of Cerium Reagents Derived from (Trimethylsilyl)propargyl Bromide to Aldehydes. In: Liebigs Annalen der Chemie. 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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