Stereochemistry in the Reactions of (Z)- and (E)-Allyltributylstannyl Reagents with Quinones

Article abstract of DOI:10.1021/jo00383a016

In the BF3-catalyzed allylation of quinones with allylstannyl reagents, (Z)-hexenyltributylstannane (3) is introduced with no retention of the original double-bond stereochemistry, and neryl reagent (5) is introduced with partial loss of olefin stereochemistry.In contrast, (E)-2-hexenyltributylstannane (4) and geranyltributylstannane (6) are introduced with complete retention of their olefin geometries.