Intramolecular rhodium-catalyzed activation of α-amino C-H bonds:: decisive influence of conformational factors in the synthesis of bicyclic aminals from N-sulfamoyloxyacetyl azacycloalkanes

The activation of alpha-amino C-H bonds in azacycloalkanes by way of intramolecular rhodium-catalyzed amination is reported. In this study, the 'activating' sulfamoyloxy group is attached to the endocyclic nitrogen atom with an appropriate linker. The influence of various structural parameters was studied. Results obtained demonstrate the remarkable conformational control that is possible with such azacycloalkane systems. This work leads to the first example of a successful intramolecular catalyzed amination of a tertiary sulfamic ester, a substrate known to be highly prone to elimination and/or nucleophilic displacement. (C) 2007 Elsevier Ltd. All rights reserved.