Joint palladium/norbornene organometallic catalysis allows for straightforward access to dibenzo[c,e]azepines. These synthetically challenging polycyclic frameworks form in one pot via a three-component coupling of an aryl iodide, a bromobenzylamine, and an olefin. A key, atroposelective aryl–aryl coupling from chelated Pd(IV) intermediates dictates the outcome of the cascade. DFT modeling sheds light on the complex mechanism that allows the complete diasteroselectivity to be observed
Diastereoselective Synthesis of Dibenzoazepines through Chelation on Palladium(IV) Intermediates / V., Narbonne; P., Retailleau; Maestri, Giovanni; M., Malacria. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 16:(2014), pp. 628-631. [10.1021/ol403525c]
Diastereoselective Synthesis of Dibenzoazepines through Chelation on Palladium(IV) Intermediates
MAESTRI, Giovanni;
2014-01-01
Abstract
Joint palladium/norbornene organometallic catalysis allows for straightforward access to dibenzo[c,e]azepines. These synthetically challenging polycyclic frameworks form in one pot via a three-component coupling of an aryl iodide, a bromobenzylamine, and an olefin. A key, atroposelective aryl–aryl coupling from chelated Pd(IV) intermediates dictates the outcome of the cascade. DFT modeling sheds light on the complex mechanism that allows the complete diasteroselectivity to be observedI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
