Alkylidenation of Ester Carbonyl Groups by means of a Reagent Derived from RCHBr2, Zn, TiCl4, and TMEDA. Stereoselective Preparation of (Z)-Alkenyl Ethers

DOI: 10.1021/jo00228a055

Source and publish data:

Journal of Organic Chemistry p. 4410 - 4412 (1987)

Update date:2022-07-29

Topics: Ester Carbonyl group Reagent Stereoselective Zn Alkylidenation TiCl4

Authors:

Okazoe, Takashi

Takai, Kazuhiko

Oshima, Koichiro

Utimoto, Kiitiro

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Article abstract of DOI:10.1021/jo00228a055

Reagents prepared by reduction of 1,1-dibromoalkanes (R³CHBr2) with zinc and TiCl4 in the presence of N,N,N',N'-tetramethylethylenediamine in THF are effective in the conversion of esters (R¹CO2R²) to the corresponding alkenyl ethers (R¹(R²O)C=CHR³) with high Z selectivity.

Full text of DOI:10.1021/jo00228a055

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