112623-39-9Relevant academic research and scientific papers
Intramolecular Ene Reactions, III. - Diastereoselective Formation of Cyclohexanes by Intramolecular Ene Reactions of 1,7-Dienes
Tietze, Lutz F.,Beifuss, Uwe
, p. 321 - 330 (2007/10/02)
The 1,7-dienes 3a-c with a double-activated enophile moiety undergo thermal and zinc bromide catalyzed intramolecular ene reactions leading to trans-1,2-disubstituted cyclohexanes 4a-c in up to 89 percent yield, highly diastereoselectively.The synthesis of cyclohexanes from 1,7-dienes has not been feasible so far in a selective way and with good yields.Reaction of 3d, 3e, and 3f gives mixtures of intramolecular hetero Diels-Alder adducts, ene and tandem ene products.The 1,7-dienes 3 are obtained by Knoevenagel condensation of 7-methyl-6-octenal (2) with acyclic 1,3-dicarbonyl and analogous compounds 1.
