The present review describes some of our recent applications of tricarbonyliron-diene chemistry to organic synthesis. It focuses on the selective synthesis of tricarbonyliron-diene complexes including the asymmetric catalytic complexation of prochiral cyclohexa-1,3-dienes, the enantioselective synthesis of carbazole-3,4-quinone alkaloids, and the iron-mediated synthesis of corannulene and yohimbane alkaloids.
The palladium-mediated intramolecular aryl amination of 7-benzyloxy-1-(2-bromo-4,5-dimethoxy-benzyl)-1,2,3,4-tetrahydro-6-methoxy-isoquinoline catalyzed by a recently discovered, air and moisture stable (NHC)Pd(h 3 -allyl)Cl (NHC = Nheterocyclic carbene) complex provides 2-benzyloxy-5,6,12,12a-tetrahydro-3,9,10-trime-thoxydibenz-[b,g]-indolizine in high yield. Effects of the solvent, the catalyst loading and the nature of the NHC-ancilliary ligand on the efficacy of the reaction were examined. Using identical conditions 7-benzyloxy-1-(2-chloro-4,5-methylendioxybenzyl)-1,2,3,4-tetrahydro-6-methoxyisoquinoline leads to 2-benzyloxy-5,6-12,12a-tetrahydro-3-methoxy-9,10-methylendioxydibenz-[b,g]-indolizine, also in high yield. Use of the catalytic intramolecular aryl amination step allows for the straightforward synthesis of the alkaloids rac-cryptaustoline and rac-cryptowoline.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.