Applications Of (E)-1,2-disubstituted Vinylstannanes In Stereoseletive Synthesis Of Trisubstituted Alkenes And 1, 3-dienes

This dissertation describes the applications of (E)-1,2-disubstituted vinystannane -s in stereoseletive synthesis of trisubstituted alkenes and 1,3-dienes.We carried out the cross-coupling reaction of (E)-α-arylvinylstannanes with acyl chlorides in the presence of Pd(PPh3)4/CuI to afford the corresponding (E) -α-aryl-α,β-unsaturated ketones. We studied the Stille cross-coupling reaction of (E)-α-stannyl-α,β-unsaturated esters with aryl iodide in the presence of Pd(PPh3)4/CuI to afford the corresponding (Z)-α-aryl-α,β-unsaturated esters in good yields. We also studied the cross-coupling reaction of (E)-α-arylvinylstannanes with alkenyl halide catalyzed by Pd(PPh3)4/CuI, which provides a new route to stereoselective synthesis of (Z,E)-2-aryl-substituted 1,3-dienes in good yields.We also carried out the tandem hydrostannylation-Stille reaction of a variety of aryl substituted alkynes with tributyltin hydride and acyl chlorides, providing one-pot stereoselective synthesis of (E)-α-aryl-α,β-unsaturated ketones. We investigated the tandem hydrostannylation-Stille reaction of alkynyl esters with tributyltin hydride and aryl halides, providing one-pot stereoselective synthesis of (Z)-α-Aryl-α,β- unsaturated esters. We also carried out the tandem hydrostannylation-Stille reaction of a variety of aryl substituted alkynes with tributyltin hydride and alkenyl halides, providing one-pot stereoselective synthesis of (Z,E)-2-aryl-substituted 1,3-dienes.