Asymmetric β-functionalization of secondary amine with CH2Cl2 on a chiral NCN pincer Rh complex

• Asymmetric C–C bond formation of an amine with CH2Cl2 by chiral NCN pincer Rh complex.
• β-functionalization of an amine via C–H bond activation and C–Cl oxidative addition.
• Determination of the absolute configuration of new chiral center by X-ray analysis.
• C–N bond formation of NEt3 with CH2Cl2 giving the ammonium ylide complex.

Functionalization of a β-C–H bond of a secondary aliphatic amine was accomplished using NCN pincer Rh complex 1 with a chiral bis(oxazolinyl)phenyl ligand. Complex 1 underwent asymmetric alkylation of dicyclopentylamine with CH2Cl2 to form azametallacycle complex 2. Additionally, the reaction of 1 with triethylamine in CH2Cl2 resulted in the formation of ammonium ylide complex 3 via C–N bond formation.

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