- De novo synthesis of troc-protected amines: Intermolecular rhodium-catalyzed C-H amination with N-tosyloxycarbamates
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The rhodium-catalyzed intermolecular C-H insertion of the nitrene derived from 2,2,2-trichloroethyl-N-tosyloxycarbamate proceeded in good to excellent yields to produce a variety of Troc-protected amines. With cyclic aliphatic alkanes, it is possible to use only 2 equiv of substrate, whereas the reaction with aromatic alkanes is run neat. Not only does the nitrene insertion proceed in benzylic, secondary, and tertiary C-H bonds but also primary C-H insertion products were obtained in good yields. Finally, the use of chiral rhodium catalysts to provide an enantioselective version of this process is discussed.
- Lebel, Helene,Kim, Huard
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p. 639 - 642
(2008/02/03)
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