477909-87-8Relevant academic research and scientific papers
Remote electronic effects in the rhodium-catalyzed nucleophilic ring opening of oxabenzonorbornadienes.
Lautens, Mark,Schmid, Gavin A,Chau, Anh
, p. 8043 - 8053 (2007/10/03)
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.
