1033950-85-4Relevant articles and documents
Synthesis of δ-tributylstannyl-α,βγ, δ-unsaturated aldehydes from pyridines
Michels, Theo D.,Rhee, Jong Uk,Vanderwal, Christopher D.
supporting information; experimental part, p. 4787 - 4790 (2009/05/07)
(Equation Presented) Zincke aldehydes, which are readily available from the ring-opening reaction of pyridinium salts, are easily converted into δ-tributylstannyl-α,β,γ,δ-unsaturated aldehydes (stannyldienals) by the action of tributylstannyllithium. This reaction appears to proceed via 1,6-stannyllithium addition/elimination of lithium dialkylamide. Several stannyldienals of significant utility for the synthesis of polyene natural products have been made by this route, which proceeds in modest yields, but is successful on multigram scale using inexpensive reagents. Simple stannylenals and stannylenones are similarly available from the corresponding vinylogous amides.