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An Improved Class of Phosphite-Oxazoline Ligands for Pd-Catalyzed Allylic Substitution Reactions

Journal article
Authors M. Biosca
J. Salto
M. Magre
Per-Ola Norrby
O. Pamies
M. Dieguez
Published in Acs Catalysis
Volume 9
Issue 7
Pages 6033-6048
ISSN 2155-5435
Publication year 2019
Published at Department of Chemistry and Molecular Biology
Pages 6033-6048
Language en
Links dx.doi.org/10.1021/acscatal.9b01166
Keywords palladium, asymmetric allylic substitution, DFT calculations, NMR study, mixed P,N-ligands, molecular-orbital methods, force-field parameters, asymmetric-synthesis, kinetic resolution, enantioselective allylation, cyclobutane backbone, modular ligands, basis-sets, ab-initio, alkylation, Chemistry, lean ad, 1980, journal of chemical physics, v72, p5639, ertus s, 1982, chemical physics, v65, p239
Subject categories Biochemistry and Molecular Biology

Abstract

A method for generation of Pd/phosphite-oxazoline catalysts containing an alkyl backbone chain has been successfully applied to Pd-catalyzed allylic substitution reactions. By carefully selecting the substituents at both the alkyl backbone chain and the oxazoline of the ligand, as well as the configuration of the biaryl phosphite group, high activities (TOF > 8000 mol substrate X (mol Pd X h)(-1)) and excellent enantioselectivities (ee's up to 99%) have been achieved for many hindered and unhindered substrates with a wide range of C-, O-, and N-nucleophiles (73 substitution products in total). Moreover, DFT and NMR studies of the key Pd-allyl complexes allowed us to better understand the origin of the excellent enantioselectivities observed experimentally. The useful application of the Pd/phosphite-oxazoline catalysts was demonstrated by the syntheses of many chiral carbobicycles, with multiples stereocenters, by simple sequential reactions involving Pd-allylic substitution and either 1,6-enyne cyclization or Pauson-Khand enyne cyclization.

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