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Screening of a phosphite-phosphoramidite ligand library for palladium-catalysed asymmetric allylic substitution reactions: the origin of enantioselectivity.
Chemistry. 2008; 14(3):944-60.C

Abstract

We have designed a new library of readily available, highly modular phosphite-phosphoramidite ligands for asymmetric allylic substitution reactions. They are easily prepared in one step from commercially available chiral 1,2-amino alcohols. The introduction of a phosphoramidite moiety into the ligand design is highly advantageous for the product outcome. This ligand library affords high reaction rates (TOFs of up to 800 mol (mol h)(-1)) and enantioselectivities (ees of up to 99%) and, at the same time, contains a broad range of disubstituted hindered and unhindered substrate types. NMR study of the Pd-pi-allyl intermediates provide a deeper understanding of the effect of the ligand parameters on the origin of enantioselectivity.

Authors+Show Affiliations

Departament de Química Física i Inorgànica, Universitat Rovira i Virgili, C/Marcel.lí Domingo s/n, 43007 Tarragona, Spain. oscar.pamies@urv.catNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

17979171

Citation

Pàmies, Oscar, and Montserrat Diéguez. "Screening of a Phosphite-phosphoramidite Ligand Library for Palladium-catalysed Asymmetric Allylic Substitution Reactions: the Origin of Enantioselectivity." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 14, no. 3, 2008, pp. 944-60.
Pàmies O, Diéguez M. Screening of a phosphite-phosphoramidite ligand library for palladium-catalysed asymmetric allylic substitution reactions: the origin of enantioselectivity. Chemistry. 2008;14(3):944-60.
Pàmies, O., & Diéguez, M. (2008). Screening of a phosphite-phosphoramidite ligand library for palladium-catalysed asymmetric allylic substitution reactions: the origin of enantioselectivity. Chemistry (Weinheim an Der Bergstrasse, Germany), 14(3), 944-60.
Pàmies O, Diéguez M. Screening of a Phosphite-phosphoramidite Ligand Library for Palladium-catalysed Asymmetric Allylic Substitution Reactions: the Origin of Enantioselectivity. Chemistry. 2008;14(3):944-60. PubMed PMID: 17979171.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Screening of a phosphite-phosphoramidite ligand library for palladium-catalysed asymmetric allylic substitution reactions: the origin of enantioselectivity. AU - Pàmies,Oscar, AU - Diéguez,Montserrat, PY - 2007/11/6/pubmed PY - 2007/11/6/medline PY - 2007/11/6/entrez SP - 944 EP - 60 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 14 IS - 3 N2 - We have designed a new library of readily available, highly modular phosphite-phosphoramidite ligands for asymmetric allylic substitution reactions. They are easily prepared in one step from commercially available chiral 1,2-amino alcohols. The introduction of a phosphoramidite moiety into the ligand design is highly advantageous for the product outcome. This ligand library affords high reaction rates (TOFs of up to 800 mol (mol h)(-1)) and enantioselectivities (ees of up to 99%) and, at the same time, contains a broad range of disubstituted hindered and unhindered substrate types. NMR study of the Pd-pi-allyl intermediates provide a deeper understanding of the effect of the ligand parameters on the origin of enantioselectivity. SN - 0947-6539 UR - https://www.unboundmedicine.com/medline/citation/17979171/Screening_of_a_phosphite_phosphoramidite_ligand_library_for_palladium_catalysed_asymmetric_allylic_substitution_reactions:_the_origin_of_enantioselectivity_ DB - PRIME DP - Unbound Medicine ER -
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