Synthesis 2003(10): 1574-1578
DOI: 10.1055/s-2003-40513
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Novel Base-Catalyzed Stereoselective Synthesis of Trifluoromethylated Dienedinitriles

Yanchang Shen*, Guoping Wang, Jiahong Ni, Jie Sun
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China
Fax: +86(21)64166128; e-Mail: shenyc@pub.sioc.ac.cn;
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Publikationsverlauf

Received 31 March 2003
Publikationsdatum:
08. Juli 2003 (online)

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Abstract

The trifluoromethylated γ-cyano-β,γ-unsaturated nitrile 4 was prepared by the reaction of bromo(cyanomethyl)zinc with trifluoroacylated phosphonate 3 in 67% yield (E:Z = 60:40). The E- and Z-isomers obtained were easily separated by column chromatography. Treatment of a catalytic amount of t-BuOK (20 mol%) with a mixture of (Z)-4 and N-toluenesulfonylimines 5 gave trifluoromethylated dienedinitriles 6 in 68-83% yields.

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