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.
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 -