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Synfacts 2011(9): 0997-0997
DOI: 10.1055/s-0030-1260889
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. WagnerR. 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
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)
Key words
rhodium - asymmetric synthesis - trifluoroborates - ketimines
Significance
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.
Comment
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.