4.8 Article

Copper-Catalyzed Enantioselective Sonogashira Type Coupling of Alkynes with α-Bromoamides

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 33, Pages 13998-14002

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202000860

Keywords

copper catalysis; enantioselectivety; Sonogashira reaction; terminal alkynes; alpha-bromoamide

Funding

  1. [NSFC-21772218]
  2. [21821002]
  3. [XDB20000000]

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An asymmetric copper-catalyzed Sonogashira type coupling between alkynes and alpha-bromoamides has been developed. This method represents a facile approach to synthetically useful beta, gamma-alkynyl amides from two readily available starting materials in a highly enantioselective manner. A Bisoxazoline diphenylanaline (BOPA) serves as the effective chiral ligand. Preliminary mechanistic studies support the formation of alkyl radical species .

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