1. Novel O,N,N,O-tetradentate ligand from tartaric acid
- Author
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Venkitasamy Kesavan, Ravichandran Vasanthan, and Kaluvu Balaraman
- Subjects
dimethyl 2 [1,3 bis(4 methoxyphenyl)allyl]malonate ,chirality ,o,n,n,o tetradentate bioxazoline ligand ,Alkylation ,proton nuclear magnetic resonance ,Biochemistry ,Tsuji–Trost reaction ,chemistry.chemical_compound ,chelation ,2 [1,3 bis(4 chlorophenyl)allyl]malononitrile ,dimethyl 2 [1,3 bis(3 chlorophenyl)allyl]malonate ,Drug Discovery ,Chemistry ,Chiral ligand ,dimethyl 2 [1,3 bis(4 fluorophenyl)allyl]malonate ,dimethyl 2 [1,3 bis(4 bromophenyl)allyl]malonate ,unclassified drug ,priority journal ,Tartaric acid ,hydrogenation ,chemical modification ,crystal structure ,Stereochemistry ,dimethyl 2 (4 phenylbut 3 en 2 yl)malonate ,asymmetric allylic alkylation ,complex formation ,enantioselectivity ,Chelation ,dimethyl 2 (1,3 diphenylallyl)malonate ,alkylation ,diethyl 2 [1,3 bis(4-chlorophenyl)allyl]malonate ,oxazoline derivative ,solvent effect ,catalysis ,dimethyl 2 [1,3 bis(4 chlorophenyl)allyl]malonate ,Ligand ,organic chemicals ,Organic Chemistry ,Enantioselective synthesis ,diethyl 2 [1,3 bis(4 chlorophenyl)allyl]malonate ,dimethyl 2 (1,3 dip tolylallyl)malonate ,carbon nuclear magnetic resonance ,palladium ,dimethyl 2 [1,3 di(naphthalen 2 yl)allyl]malonate ,tartaric acid ,substitution reaction ,chemical structure ,dimethyl 2 [1,3 bis(3 bromophenyl)allyl]malonate ,3 [1,3 bis(4 chlorophenyl)allyl]pentane 2,4 dione ,Tetradentate ligand - Abstract
A new class of highly stable O,N,N,O-tetradentate bioxazoline ligands were synthesized from l-tartaric acid. Exploration of those ligands in Pd-catalyzed asymmetric allylic alkylation yielded alkylated product up to 96% ee. Necessity of additional chelation to obtain high enantioselectivity was also demonstrated. Structural modifications of this ligand might result in identification of a novel privileged chiral ligand from an inexpensive chiral pool. � 2013 Elsevier Ltd. All rights reserved.
- Published
- 2013
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