Original scientific paper

Comparative Study of 1,5-Dinitrogen Schiff Bases as Potential Ligands in Palladium-Catalyzed Allylic Alkylation

Dragan Šepac ; Ruđer Bošković Institute, P.O.B. 180, 10002 Zagreb, Croatia
Marin Roje ; Ruđer Bošković Institute, P.O.B. 180, 10002 Zagreb, Croatia
Zdenko Hameršak ; Ruđer Bošković Institute, P.O.B. 180, 10002 Zagreb, Croatia
Vitomir Šunjić ; Ruđer Bošković Institute, P.O.B. 180, 10002 Zagreb, Croatia

Abstract

1-(2'-Pyrido and 2'-quinolino)-(1R)-arylethylamino)-ethylidenes (7–12) were prepared as potential ligands in PdII catalytic complexes for enantioselective allylic alkylation of 1,3-diphenyl-1-acetoxy-propene-2 (15). Alkylation with palladium complexes of 7–12 yielded 1,3-diphenyl-1-dimethylmalonyl-propene-2 (14) with enantioselectivity up to 55 % e.e. Enantioselectivity is discussed in view of the results recently reported for structurally related 1,5-bidentate dinitrogen ligands of C₁ symmetry. Reversal of enantioselectivity observed for the ligands 10 and 11 is attributed to the inversion of steric requirements in the second coordination sphere of their catalytic complexes.

Keywords

ethylidenes; conformation; Pd^II complexes; allylic alkylation

Hrčak ID:

103173

URI

https://hrcak.srce.hr/103173

Publication date:

29.8.2003.

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