Chiral Diamine-Copper(I) Complexes as Asymmetric Catalysts in the Enantioselective Addition of Phenylacetylene to Imines

Abstract

The stereoselective addition of phenyl acetylene to im­ines, catalysed by chiral bis-amine-Cu(I) complexes was studied. The chiral ligands are either commercially available or easily prepared in one or two steps. This very convenient and extremely simple experimental procedure at room temperature allowed optically active propargyl amines to be obtained in good yields with enantio­selectivities up to 70%.

Key words

chiral bis-amines - copper complexes - propargyl­amines - enantioselective catalysis - acetylene addition

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16

(1R,2R)-1,2-trans-Diaminocyclohexane and (1R,2R)-1,2-diaminodiphenylethylenediamine were also tested as chiral ligands, but with modest results.

17

For reactions promoted by chiral diamine complexes in aqueous solvents, see ref. 15c and 15d.

18

The reaction also worked in MeCN-H₂O, 9:1 (51% yield, 18% ee).

21

N-Benzyl- and N-alkylimines did not react under our reaction conditions.