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Article Dans Une Revue Angewandte Chemie International Edition Année : 2020

Enantioselective Synthesis of N–C Axially Chiral Compounds by Cu‐Catalyzed Atroposelective Aryl Amination

Résumé

N−C axially chiral compounds have emerged recently as appealing motifs for drug design. However, the enantioselective synthesis of such molecules is still poorly developed and surprisingly no metal‐catalyzed atroposelective N‐arylations have been described. Herein, we disclose an unprecedented Cu‐catalyzed atroposelective N−C coupling that proceeds at room temperature. Such mild reaction conditions, which are a crucial parameter for atropostability of the newly generated products, are operative thanks to the use of hypervalent iodine reagents as a highly reactive coupling partners. A large panel of the N−C axially chiral compounds was afforded with very high enantioselectivity (up to >99 % ee) and good yields (up to 76 %). Post‐modifications of thus accessed atropisomeric compounds allows further expansion of the diversity of these appealing compounds.
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Dates et versions

hal-03065996 , version 1 (15-12-2020)

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Johanna Frey, Alaleh Malekafzali, Isabel Delso, Sabine Choppin, Françoise Colobert, et al.. Enantioselective Synthesis of N–C Axially Chiral Compounds by Cu‐Catalyzed Atroposelective Aryl Amination. Angewandte Chemie International Edition, 2020, 59 (23), pp.8844-8848. ⟨10.1002/anie.201914876⟩. ⟨hal-03065996⟩
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