66169-66-2Relevant academic research and scientific papers
1,3-Difunctionalization of Aminocyclopropanes via Dielectrophilic Intermediates
Wang, Ming-Ming,Waser, Jér?me
supporting information, p. 13880 - 13884 (2019/08/30)
We report an oxidative ring-opening strategy to transform acyl, sulfonyl or carbamate protected aminocyclopropanes into 1,3-dielectrophilic carbon intermediates bearing a halide atom (Br, I) and a N,O-acetal. Replacing the alkoxy group of the N,O-acetal can be achieved under acidic conditions through an elimination–addition pathway, while substitution of the halides by nucleophiles can be done under basic conditions through a SN2 pathway, generating a wide range of 1,3-difunctionalized propylamines. A proof of concept for asymmetric induction was realized using a chiral phosphoric acid (CPA) as catalyst, highlighting the potential of the method in enantioselective synthesis of important building blocks.
