- A General Method for the Synthesis of 2-Alkyl Substituted 1,3-Dienes Starting from 2-(Chloromethyl)-3-tosylpropene
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The alkylation of the monolithium derivative 5 of 2-(chloromethyl)-3-tosylpropene (1) with bromo- or iodo-methyltrimethylsilane affords the β-silyl sulfone 7, which after nucleophilic substitution of the chlorine atom followed by β-elimination of tosyltrimethylsilane, promoted by tetrabutylammonium fluoride (TBAF), gives 2-substituted conjugated dienes 6 and the outer-ring diene 14.Racemic ipsenol (10b), an aggregation pheromone of the bark beetle Ips paraconfusus Lanier, is prepared.
- Najera, Carmen,Sansano, Jose Miguel
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p. 5829 - 5844
(2007/10/02)
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- 2-(Chloromethyl)-3-tosylpropene as useful reagent for the general synthesis of functionalized 2-substituted 1,3-dienes. Application to the synthesis of (±)-ipsenol
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The reaction of the monolithium derivative of 2-(chloromethyl)-3-tosylpropene (2) with bromomethyltrimethylsilane affords the β-silyl sulfone 7, which after nucleophilic substitution followed by fluoride induced β-elimination of tosyltrimethylsilane gives 2-substituted conjugated dienes 1. When compound 7 reacts first with zinc in the presence of isovaleraldehyde and then with tetrabutylammonium fluoride racemic ipsenol (10), an aggregation pheromone of the bark beetle Ips paraconfusus Lanier, is prepared.
- Najera,Sansano
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p. 3781 - 3784
(2007/10/02)
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