4.8 Article

Palladium-Catalyzed Regio- and Enantioselective Synthesis of Allylic Amines Featuring Tetrasubstituted Tertiary Carbons

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 43, Pages 14194-14197

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b08841

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Funding

  1. ICIQ
  2. ICREA
  3. Spanish MINECO [CTQ-2014-60419-R]
  4. Severo Ochoa Excellence Accreditation [SEV-2013-0319]
  5. Cellex Foundation
  6. ICREA Funding Source: Custom

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The first asymmetric synthesis of alpha,alpha-disubstituted allylic N-arylamines based on a palladium catalyzed allylic amination has been developed. The protocol uses highly modular vinyl cyclic carbonates and unactivated aromatic amine nucleophiles as substrates. The catalytic process features minimal waste production, ample scope in reaction partners, high asymmetric induction up to 97% ee, and operational simplicity.

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