ChemInform Abstract: Rh/Pd Catalysis with Chiral and Achiral Ligands: Domino Synthesis of Aza‐Dihydrodibenzoxepines.

Abstract

Rh/Pd Catalysis with Chiral and Achiral Ligands: Domino Synthesis of Aza-Dihydrodibenzoxepines. -The preparation of aza-dihydrodibenzoxepines is described, through the combination of Rh-catalyzed arylation and Pd-catalyzed C-O coupling in a single pot. The domino reactivity depends on the electronics of the vinyl pyridine, with electron-poor vinyl pyridines producing optimal conversion into the desired products. A two-step process is developed for those substrates that do not proceed to full conversion. Additionally, an asymmetric variant of the reaction is presented. For the first time, the ability to incorporate a chiral and an achiral ligand in the same pot is achieved, giving the products in moderate to good yields, with excellent enantioselectivities. -(FRIEDMAN, A. A.; PANTELEEV, J.; TSOUNG, J.; HUYNH, V.; LAUTENS*, M.; Angew. Chem., Int. Ed. 52 (2013) 37, 9755-9758, http://dx.doi.org/10.1002/anie.201303659 ; Davenport Res. Lab., Dep. Chem., Univ. Toronto, Toronto, Ont. M5S 3H6, Can.; Eng.) -Bartels 07-209