Letters in Organic Chemistry

Author(s): David Rodriguez-Lucena, Marie S.T. Morin and Philippe Compain

DOI: 10.2174/157017811795038340

DownloadDownload PDF Flyer Cite As
Concise Synthesis of Bicyclic Aminals by Way of Catalytic Intramolecular C-H Amination and Evaluation of Their Reactivity as Iminium Precursors

Page: [155 - 162] Pages: 8

  • * (Excluding Mailing and Handling)

Abstract

The concise synthesis of fused bicyclic aminals by way of intramolecular rhodium-catalyzed C-H amination is reported as well as the evaluation of their reactivity as iminium precursors. In contrast to the well-studied N,O-acetal systems, the aminals synthesized were found to be particularly stable under reaction conditions used for nucleophilic addition.

Keywords: C-H amination, aminal, iminium, azacycloalkane, nucleophilic addition, regioselectivity, sulfamate, heterocycles, multifunctionalization, diastereoselectivity