A highly selective synthesis of versatile (E)-1-phenylthio vinylstannanes

Asymmetric Claisen Rearrangements on Chiral Vinyl Sulfoxides

“…[24] Then, syn Pd-catalyzed hydrostannylation provided vinyl stannanes 8 a,c,d in good yields. [25] Further transmetallation with nBuLi and addition to benzaldehyde or acetone provided a-hydroxy vinyl sulfides 10 a,c,d or 14 a,c as racemic materials. In addition, the synthesis of 10 e (R 2 = Ph) was accomplished by direct deprotonation of vinyl sulfide 9 a followed by addition of the lithium carbanion onto propionaldehyde.…”

A One‐pot, Stereoselective Synthesis of (Z)‐2‐Sulfonyl‐Substituted 1,3‐Enynes by Hydrostannylation‐Stille Tandem Reaction of Acetylenic Sulfones

“…Palladium-catalyzed hydrostannylation of phenylthioalkynes, 17 alkynyl selenides, 18 and alkynyl sulfoxides 19 has been reported to be highly regio-and stereoselective, providing a direct route for the stereoselective synthesis of 1,1-difunctional group reagents containing heteroatom and tin. Xiang and coworkers reported that palladium-catalyzed hydrostannylation of acetylenic triflones with tributyltin hydride provided α-stannylated vinyl triflones regiospecifically, however the reaction was not stereospecific and afforded a 1∶1.7 ratio of E and Z stereoisomers.…”

A novel stereoselective synthesis of (2Z)‐2‐arylsulfanylallylic alcohols by tin–lithium exchange of (E)‐α‐stannylvinyl sulfides

“…(E)-α-Stannylvinyl sulfides 1 were prepared regioand stereoselectively by the palladium-catalyzed hydrostannylation reaction of alkynylsulfides according to a literature procedure [40]. (E)-α-Stannylvinyl sulfides 1 are very useful difunctional group reagents in which two synthetically versatile groups are linked to the same olefinic carbon atom and can be considered both as vinylstannanes and as vinyl sulfides.…”