Synfacts 2011(9): 0997-0997  
DOI: 10.1055/s-0030-1260889
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Rh-Catalyzed Asymmetric Addition of Trifluoroborates to Sulfonylketimines

Contributor(s):Paul Knochel, Andreas J. Wagner
R. Shintani*, M. Takeda, Y.-T. Soh, T. Ito, T. Hayashi*
Kyoto University, Japan
Rhodium-Catalyzed Asymmetric Addition of Potassium Organotrifluoroborates to N-Sulfonyl Ketimines
Org. Lett.  2011,  13:  2977-2979  
Further Information

Publication History

Publication Date:
19 August 2011 (online)


Easily accessible potassium orga­notrifluoroborates undergo a rhodium-catalyzed asymmetric addition to both N-tosyl and N-nosyl ketimines. The use of a chiral bicyclooctadiene-based ligand allows high enantiomeric excess in the product formation.


In the case of nosyl groups, the addition products can easily be deprotected using thiophenolpotassium carbonate, retaining the enantiomeric purity. For related applications of dienic ligands, see: K. Okamoto, T. Hayashi, V. H. Rawal Org. Lett. 2008, 10, 4387.