Diastereoselective Catalytic C-H Amination

Key words

C-H activation - amination - rhodium

Significance

The metal-mediated direct amination through C-H bond insertion is a very powerful transformation. It usually requires a metal nitrene species which undergoes C-H insertion into the most nucleophilic C-H bond. Herein, the authors report their preliminary results of a diastereoselective version of this reaction applied to acyclic substrates of type 1, proceeding with an excellent degree of selectivity and high yields.

Comment

The authors found that especially substrates with bigger substituents [X = PO(OEt)₂, SO₂Ph] gave the best selectivities. An important feature is that the C-H amination process does not affect the configuration of the stereogenic center in β-position when the reaction was carried out with enantiomerically pure starting material. Furthermore, a possible explanation for the dia­stereoselective outcome of the transformation has been assumed by considering the staggered conformer A to be more favored than conformer B due to dipole repulsion.