4.8 Article

Enantiomerically pure rhodium complexes bearing 1,5-diphenyl-1,5-cyclooctadiene as a chiral diene ligand. Their use as catalysts for asymmetric 1,4-addition of phenylzinc chloride

Journal

ORGANIC LETTERS
Volume 7, Issue 26, Pages 5889-5892

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol0524914

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A rhodium complex coordinated with 1,5-diphenyl-1,5-cyclooctadiene (Ph-cod), [RhCl((R)-Ph-cod)](2), was obtained enantiomerically pure through optical resolution of diastereomeric isomers [Rh(Ph-cod)((R)-1,1'-binaphthyl-2,2'-diamine)]BF4. The enantiomerically pure rhodium complexes showed high catalytic activity and enantioselectivity (up to 98% ee) in the asymmetric 1,4-addition of phenylzinc chloride to alpha,beta-unsaturated ketones and esters in the presence of chlorotrimethylsilane.

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