134962-99-5Relevant articles and documents
Prenylation reaction performed with catalytically generated potassium prenal dienolate
Cahard, Dominique,Duhamel, Lucette,Lecomte, Sandrine,Poirier, Jean-Marie
, p. 1399 - 1401 (2007/10/03)
A new prenylation method based on the reaction of catalytically generated potassium dienolate of prenal with α,β-unsaturated aldehydes is described. The reaction is highly regioselective, via a γ-1,2-addition, and provides an efficient route to retinal.
A new prenylation method using the lithium enolate of prenal. Reaction with polyunsaturated aldehydes. A short access to retinal
Duhamel, Lucette,Guillemont, Jerome,Poirier, Jean-Marie,Chabardes, Pierre
, p. 4499 - 4500 (2007/10/02)
The enolate of prenal 1 prepared from the corresponding silyl enol ether 2 or enol acetate 3 led to a γ-regiospecific reaction with polyunsaturated aldehydes 4 yielding dihydropyrans 5 leading after hydrolysis to polyenals 7. This process allows the introduction of the isoprenyl skeleton. A synthesis of retinal, from β-ionylidenacetaldehyde is reported.