Iron-Catalyzed Regio- and Stereoselective Carbolithiation of Alkynes

Iron-Catalyzed Regio- and Stereoselective Carbolithiation of Alkynes

Butylation problems ironed out: 3‐Pentynyl ethers react with butyllithium at −20°C in toluene, upon addition of a catalytic amount of a cheap iron(III) salt, to afford (E)‐4‐methyl‐3‐octenyl ethers in high yields. Stereochemically defined tetrasubstituted alkenes were also obtained by the subsequent...

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Veröffentlicht in:Angewandte Chemie International Edition 2001-02, Vol.40 (3), p.621-623
Hauptverfasser: Hojo, Makoto, Murakami, Yoshio, Aihara, Hidenori, Sakuragi, Rie, Baba, Yu, Hosomi, Akira
Format: Artikel
Sprache:eng
Schlagworte:
alkenes
homogeneous catalysis
iron
lithium
nucleophilic addition
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Zusammenfassung:Butylation problems ironed out: 3‐Pentynyl ethers react with butyllithium at −20°C in toluene, upon addition of a catalytic amount of a cheap iron(III) salt, to afford (E)‐4‐methyl‐3‐octenyl ethers in high yields. Stereochemically defined tetrasubstituted alkenes were also obtained by the subsequent addition of electrophiles (E+, see scheme; acac = acetylacetonate, Bn=benzyl).
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20010202)40:3<621::AID-ANIE621>3.0.CO;2-O