Remote electronic effects in the rhodium-catalyzed nucleophilic ring opening of oxabenzonorbornadienes.
We report the application of our rhodium-catalyzed nucleophilic ring-opening methodology to unsymmetrically arene-substituted oxabenzonorbornadienes. The regioselectivity of the ring opening was investigated using a variety of nucleophiles that led to a broad selection of dihydronaphthalene products. It was found that good to excellent regioselectivities are obtained using strongly pi-donating substituents, whereas sigma-donating and electron-withdrawing functionalities have a minimal effect. Post ring-opening manipulations of functional groups in the dihydronaphthalene products were shown to give efficient access to mono- and diamine tetrahydronaphthalene building blocks.
Lautens
Mark
M
Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5H 3H6. mlautens@chem.utoronto.ca
Schmid
Gavin A
GA
Chau
Anh
A
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry; D002384:Catalysis; D004583:Electrons; D009281:Naphthalenes / Q000737:chemistry; D009636:Norbornanes / Q000737:chemistry*; D012238:Rhodium; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D009281:Naphthalenes; D009636:Norbornanes; D012238:Rhodium