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1,3-Difunctionalization of Aminocyclopropanes via Dielectrophilic Intermediates.
Journal article

1,3-Difunctionalization of Aminocyclopropanes via Dielectrophilic Intermediates.

  • Wang MM Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015, Lausanne, Switzerland.
  • Waser J Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015, Lausanne, Switzerland.
  • 2019-07-18
Published in:
  • Angewandte Chemie (International ed. in English). - 2019
1,3-dielectrophile intermediate
amines
aminocyclopropanes
ring-opening
synthetic methodology
English 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 SN 2 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.
Language
  • English
Open access status
closed
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Persistent URL
https://sonar.ch/global/documents/37832
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