Highly stereo- and regioselective palladium-catalyzed syntheses of (3E,Z)-,(3E,5E)-, and (3Z,5E)-1,3,5-undecatriene

Add time:09/08/2019    Source:sciencedirect.com

(3E,5Z)-1,3,5-Undecatriene (3) having 98.2% stereoisomeric purity has been prepared by a new and expeditious route involving two selective Pd-catalyzed carbon-carbon bond forming reactions. The key step of this synthesis is a highly diastereoselective Pd-catalyzed cross-coupling reaction between 1-heptynylzinc chloride (11a) and a molar excess of (E)/(Z)-1,2-dibromoethylene (12). Another highly diastereoselective Pd-catalyzed reaction, which involves a cross-coupling between trimethylsilylethynylzinc chloride (15) and molar excesses of stereoisomeric mixtures of 1-bromo-1-alkenes (16), has been used to prepare (E)-1-trimethylsilyl-3-nonen-1-yne (10a), a key intermediate for the synthesis of (3E,5E)- and (3Z,5E)-1,3,5-undecatriene, (4) and (5). Compounds 3 and 4, isolated from the essential oil of Ferula galbaniflua, also occur together with compound 5 in the male attracting oils of seaweeds. These substances have odors highly appreciated in perfumery.

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