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White DR, Wolfe JP. Stereocontrolled Synthesis of Amino-Substituted Carbocycles by Pd-Catalyzed Alkene Carboamination Reactions. Chemistry. 2017;23(23):5419-5423doi: 10.1002/chem.201700466.
White, D. R., & Wolfe, J. P. (2017). Stereocontrolled Synthesis of Amino-Substituted Carbocycles by Pd-Catalyzed Alkene Carboamination Reactions. Chemistry (Weinheim an der Bergstrasse, Germany), 23(23), 5419-5423. https://doi.org/10.1002/chem.201700466
White, Derick R, and Wolfe, John P. "Stereocontrolled Synthesis of Amino-Substituted Carbocycles by Pd-Catalyzed Alkene Carboamination Reactions." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 23,23 (2017): 5419-5423. doi: https://doi.org/10.1002/chem.201700466
White DR, Wolfe JP. Stereocontrolled Synthesis of Amino-Substituted Carbocycles by Pd-Catalyzed Alkene Carboamination Reactions. Chemistry. 2017 Apr 24;23(23):5419-5423. doi: 10.1002/chem.201700466. Epub 2017 Apr 03. PMID: 28295688.
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Chemistry. 2017 Apr 24;23(23):5419-5423. doi: 10.1002/chem.201700466. Epub 2017 Apr 03.

Stereocontrolled Synthesis of Amino-Substituted Carbocycles by Pd-Catalyzed Alkene Carboamination Reactions.

Chemistry (Weinheim an der Bergstrasse, Germany)

Derick R White, John P Wolfe

Affiliations

  1. Department of Chemistry, University of Michigan, 930 N. University Ave., Ann Arbor, MI, 48109-1055, USA.

PMID: 28295688 DOI: 10.1002/chem.201700466

Abstract

Amino-substituted alkylidenecyclopentanes were synthesized through a stereoselective intermolecular Pd-catalyzed alkene carboamination reaction between alkenyl triflates bearing a pendant alkene and exogenous amine nucleophiles. The reactions are effective with a range of different substrate combinations, and proceed with generally high diastereoselectivity. Use of (S)-tBuPhox as the ligand in reactions of achiral substrates provides enantioenriched products with up to 98.5:1.5 e.r.

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: asymmetric catalysis; carbocycles; enantioselective synthesis; palladium; stereoselective synthesis

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