Skip to the main content

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


Full text: english pdf 181 Kb

page 235-239

downloads: 511

cite


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<sup>II</sup> complexes, allylic alkylation

Hrčak ID:

103173

URI

https://hrcak.srce.hr/103173

Visits: 852 *