P‐Chiral Monodentate Diamidophosphites − New and Efficient Ligands for Palladium‐Catalysed Asymmetric Allylic Substitution
- 27 April 2004
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 2004 (10) , 2214-2222
- https://doi.org/10.1002/ejoc.200300694
Abstract
Novel P*‐monodentate diamidophosphite ligands have been prepared by a one‐step phosphorylation of alcohols or amines. Both the electronic and the steric demands of the ligands have been estimated quantitatively. Neutral [Pd(allyl)Cl(L)] and cationic [Pd(allyl)(L)2]+ BF4− complexes have been obtained by starting from [Pd(allyl)Cl]2. The new ligands have demonstrated high enantioselectivity in the Pd‐catalysed allylic substitution reactions of 1,3‐diphenylallyl acetate with NaSO2pTol (up to 97% ee), PhCH2NH2 (up to 95% ee) and CH2(CO2Me)2 (up to 97% ee). Application of the P*‐monodentate diamidophosphites to the asymmetric catalytic synthesis of chiral carborane derivatives has also been demonstrated. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)Keywords
This publication has 44 references indexed in Scilit:
- Palladium-catalysed enantioselective synthesis of IbuprofenJournal of Molecular Catalysis A: Chemical, 2003
- Chiral P*-monodentate phosphite ligand for Pd-catalysed asymmetric allylation reactionsMendeleev Communications, 2003
- Novel Biphenol Phosphoramidite Ligands for the Enantioselective Copper-Catalyzed Conjugate Addition of Dialkyl zincsSynlett, 2001
- Sterically Crowded, Rigid,C3Symmetric Phosphites: Synthesis, Structure, and Preparation of Metal ComplexesInorganic Chemistry, 2001
- Highly Enantioselective Rh-Catalyzed Hydrogenation Reactions Based on Chiral Monophosphite LigandsPublished by Wiley ,2000
- ESPHOS and SEMI-ESPHOS: A New Family of Mono- and Bidentate Diazaphospholidine Ligands for Asymmetric CatalysisThe Journal of Organic Chemistry, 1999
- A Practical Method for the Large-Scale Synthesis of Diastereomerically Pure (2R,5S)- 3-Phenyl-2-(8-quinolinoxy)- 1,3-diaza-2-phosphabicyclo-[3.3.0]-octane Ligand (QUIPHOS). Synthesis and X-ray Structure of Its Corresponding Chiral π-Allyl Palladium ComplexThe Journal of Organic Chemistry, 1999
- Enantioselective allylic substitution catalyzed by an iridium complex: remarkable effects of the counter cationChemical Communications, 1999
- Asymmetric synthesis. Asymmetric catalytic allylation using palladium chiral phosphine complexesJournal of the American Chemical Society, 1985
- Acetylenes and noble metal compounds. Part XI. Reactions of di-methyl acetylenedicarboxylate with dibenzylideneacetone–palladium and –platinum complexes: pallada- and platina-cyclopentadienesJ. Chem. Soc., Dalton Trans., 1974