Z-Selective Synthesis of Homoallylic Alcohols via 2-Alkenylation of Aldehydes by 1-(Tributylstannyl)-2-alkene

Article abstract of DOI:10.1246/cl.1994.897

1-(Tributylstannyl)-2-alkene reacts with a solution of an aldehyde and BuSnCl3 to give (Z)-homoallylic alcohol.Z-Selective 2-methyl-2-butenylation can be accomplished by using (Z)-2-methyl-1-(tributylstannyl)-2-butene instead of 1-(tributylstannyl)-2-alkene.This reaction is useful as a new method to make (Z)-double bond.An application ot the present method for a synthesis of pheromones is also described.