4.7 Article

A Chiral Disulfoxide Ligand for the Efficient Rhodium-Catalyzed 1,2-Addition of Arylboroxines to N-Tosylarylimines

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 358, Issue 11, Pages 1759-1766

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201500975

Keywords

1; 2-additions; chiral disulfoxide ligands; diarylmethylamines; rhodium catalysis

Funding

  1. Australian Research Council (ARC) [FT130101713]
  2. University of Western Australia
  3. Australian Postgraduate Award
  4. Safety-Net Top-Up Scholarship
  5. Swiss National Science Foundation

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Enantiomerically pure diarylmethylamines are important building blocks in active pharmaceutical ingredients. Herein, we report a rhodium precatalyst with a chiral disulfoxide ligand that effects the 1,2-addition of arylboroxines to aromatic imines to give high yields and high enantioselectivities of these products. The present paper describes a system that is very simple, where the ease of synthesis of the chiral ligand is combined with low catalyst loadings and reaction conditions that do not need any additives or external base.

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