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

PDF - Published Version Download (185kB)

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 title Project leader Project code Project type Stereoselektivna sinteza i kataliza Zdenko Hameršak 0098050 MZOS
Depositing User:	Zdenko Hameršak
Date Deposited:	15 Nov 2013 12:30
URI:	http://fulir.irb.hr/id/eprint/952

Actions (login required)

View Item