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Comparative study of 1,5-dinitrogen Schiff bases as potential ligands in palladium-catalyzed allylic alkylation

Šepac, Dragan; Roje, Vibor; Hameršak, Zdenko; Šunjić, Vitomir (2003) Comparative study of 1,5-dinitrogen Schiff bases as potential ligands in palladium-catalyzed allylic alkylation. Croatica Chemica Acta, 76 (3). pp. 235-239. ISSN 0011-1643

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Abstract

1-(2'-Pyrido and 2'-quinolino)-(1R)-arylethylamino)-ethylidenes (7-12) were prepared as potential ligands in Pd-II 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 C-1 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.

Item Type: Article
Uncontrolled Keywords: ethylidenes; conformation; Pd-II complexes; allylic alkylation; enantioselective catalysis; oxazoline ligands; chiral enamines; complexes; substitutions; acids
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Projects:
Project titleProject leaderProject codeProject type
Stereoselektivna sinteza i katalizaZdenko Hameršak0098050MZOS
Depositing User: Zdenko Hameršak
Date Deposited: 15 Nov 2013 12:30
Last Modified: 27 Feb 2014 13:21
URI: http://fulir.irb.hr/id/eprint/952

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