4.8 Article

Highly Enantioselective Synthesis of Chiral Secondary Amines by Gold(I)/Chiral Bronsted Acid Catalyzed Tandem Intermolecular Hydroamination and Transfer Hydrogenation Reactions

Journal

ORGANIC LETTERS
Volume 11, Issue 18, Pages 4204-4207

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol901443b

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Funding

  1. University of Hong Kong
  2. Hong Kong Research Grants Council [HKU 1/CRF/08, HKU 7007/08P]
  3. University Grants Committee of Hong Kong [AoE/P-10/01]

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A method for the synthesis of enantiomerically enriched secondary amines with excellent ee values through the tandem intermolecular hydroamination/transfer hydrogenation of alkynes using a gold(I) complex-chiral Bronsted acid protocol is developed. The catalysis works for a wide variety of aryl, alkenyl, and aliphatic alkynes as well as anilines with different electronic properties.

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