ChemInform Abstract: The Use of Phosphine Ligands to Control the Regiochemistry of Pd‐Catalyzed Hydrostannations of 1‐Alkynes: Synthesis of (E)‐1‐Tributylstannyl‐1‐alkenes.

Abstract

The Use of Phosphine Ligands to Control the Regiochemistry of Pd-Catalyzed Hydrostannations of 1-Alkynes: Synthesis of (E)-1-Tributylstannyl-1-alkenes. -Palladium-catalyzed hydrostannylation of terminal alkynes (I) is strongly influenced by the nature of phosphine ligand used. Thus, the title E-stannylalkenes (III) are obtained with high to excellent regioselectivity in the presence of ligands like PCy3, tBu3P or tBu2P-CH2-tBu. This is successfully applied for a short synthesis of pheromone (VII). In contrast, the regioselectivity is significantly diminished in the presence of PPh3. -(DARWISH, A.; LANG, A.; KIM, T.; CHONG*, J. M.; Org. Lett. 10 (2008) 5, 861-864; Guelph-Waterloo Cent. Grad. Work Chem., Univ. Waterloo, Waterloo, Ont. N2L 3G1, Can.; Eng.) -Mischke 31-194