One-pot stereoselective synthesis of trifluoromethylated penta-(2Z,4E )-dienenitriles via double olefination
Shen, Yanchang; Ni, Jiahong; Li, Ping; Sun, Jie
Журнал:
Journal of the Chemical Society, Perkin Transactions 1
Дата:
1999
Аннотация:
A novel double olefination via sequential transformation of diethyl (1-cyanoethyl)phosphonate and its application to the synthesis of substituted trifluoromethylated pentadienenitriles with 2Z,4E-isomers formed exclusively in 71â 85% yield are described. This reaction is of broad scope since R may be alkyl, aryl or a heterocyclic group. The configuration of the products was ascertained on the basis of X-ray crystallographic analysis. The stereochemical results are rationalized by the proposed mechanism.
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