1374793-22-2Relevant academic research and scientific papers
Scalable synthesis of enantiomerically pure bicyclo[2.2.2]octadiene ligands
Abele, Stefan,Inauen, Roman,Spielvogel, Dirk,Moessner, Christian
experimental part, p. 4765 - 4773 (2012/08/08)
An operationally simple and scalable synthesis of enantiomerically pure bicyclo[2.2.2]octadiene (bod) ligands relying on an organocatalytic one-pot Michael addition-aldol reaction with cheap 2-cyclohexenone and phenylacetaldehyde is presented. The crystalline bicyclic product 4a (6-hydroxy-5-phenylbicyclo[2.2.2]octan-2-one) is transformed into phenylbicyclo[2.2.2]oct-5-en-2-one 2, a versatile starting material for the 2-step synthesis of both symmetrical, such as Hayashi's Ph-bod* ligand, as well as novel unsymmetrical chiral dienes.
