Orthopalladated complexes as phase-transfer catalysts for asymmetric alkylation of achiral Schiff base esters

Title
Orthopalladated complexes as phase-transfer catalysts for asymmetric alkylation of achiral Schiff base esters
Authors
김대현임진규김대원이현주김홍곤김훈식정민석Deb Kumar Mukherjee
Issue Date
2010-11
Publisher
Transition metal chemistry
Citation
VOL 35, NO 8, 949-957
Abstract
The asymmetric C-alkylation of benzophenone Schiff base glycine esters has been achieved using a palladium( II) chiral complex as a phase-transfer catalyst. The aromatic moiety around the metal center and various physicochemical parameters were investigated to study their effect on the asymmetric alkylation reaction under phasetransfer conditions. Moderate enantioselectivity(30–40%) was achieved under room temperature conditions, which is a significant improvement compared to no enantioselectivity with a chiral palladium-salen complex reported earlier. Computer simulation studies indicate that coordination of the metal center with Z-enolate forming a square planar complex provides a favorable steric environment where the a-carbon atom of the enolate is available for enantioselective alkylation.
URI
http://pubs.kist.re.kr/handle/201004/38096
ISSN
0340-4285
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