Practical, stereocontrolled synthesis of polyfluorinated artificial pyrethroids.
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概要
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Practical and stereocontrolled approaches to polyfluorinated synthetic pyrethroids based on aldehyde addition of CF<SUB>3</SUB>CCl<SUB>2</SUB>ZnCl are described. The zinc reagent was allowed to react with 3-formyl-2,2-dimethylcyclopropanecarboxylates (<B>6</B>) to give the corresponding adducts. These were acetylated and then reduced again with zinc to afford (1<I>R</I><SUP>*</SUP>, 3<I>S</I><SUP>*</SUP>)-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylates (<B>12</B>). The (1<I>R</I><SUP>*</SUP>, 3<I>R</I><SUP>*</SUP>)-isomer was derived from 2,2-dichloro-1,1,1-trifluoro-5-methyl-4-hexen-3-ol by diazoacetylation, Cu(II)-catalyzed intramolecular carbene addition, and finally by the zinc reduction. An alternative access to <B>12</B> and its halogen homologues of the (<I>Z</I>)-pyrethroids involves addition of 1-halo-2,2-difluoroethenyl group across the CHO group of <B>6</B> and subsequent regio- and stereoselective halogenation.
- 公益社団法人 日本化学会の論文
著者
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Hiyama Tamejiro
Sagami Chemical Research Center
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KONDO Kiyosi
Sagami Chemical Research Center
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Fujita Makoto
Sagami Chemical Research Center
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