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- Title
1,3‐Difunctionalization of Aminocyclopropanes via Dielectrophilic Intermediates.
- Authors
Wang, Ming‐Ming; Waser, Jérôme
- Abstract
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.
- Subjects
ALKOXY group; PHOSPHORIC acid; PROOF of concept; NUCLEOPHILES; HALIDES; RING-opening reactions
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 39, p14018
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201907060