Intramolecular enantioselective hydroamination catalyzed by rare earth binaphthylamides |
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Authors: | Jé rô me Hannedouche,Jacqueline Collin,Alexander Trifonov |
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Affiliation: | a Univ Paris-Sud, Laboratoire de Catalyse Moléculaire, ICMMO, UMR 8182, Orsay, F-91405, France b CNRS, Orsay, F-91405, France c G. A. Razuvaev Institute of Organometallic Chemistry of Russian Academy of Sciences, Tropinina 49, 603950 Nizhny Novgorod GSP-445, Russia |
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Abstract: | Asymmetric intramolecular hydroamination reaction is a stately way to prepare chiral nitrogen-containing heterocyclic compounds. We report in this account our personal contribution in this field with the synthesis of chiral amido rare-earth complexes. A new family of structurally defined heterobimetallic rare earth lithium ate complexes based on N-substituted binaphthylamido ligands was discovered that promoted the hydroamination/cyclization of aminoolefins with up to 87% ee.Neutral rare earth amido and amido alkyl complexes could also be prepared and led to very active species. A more simple and reliable synthetic procedure was discovered towards the preparation of heterobimetallic rare earth amido alkyl ate complexes. They proved to be also active and enantioselective catalysts, as a good compromise between efficiency and practicability issues. |
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Keywords: | Asymmetric intramolecular hydroamination Carbon-nitrogen bond formation Catalysis Amines Lanthanides Pyrrolidines |
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