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Chiral phosphaalkene-oxazoline ligands for the palladium-catalyzed asymmetric allylic alkylation.
Org Lett. 2010 Oct 15; 12(20):4667-9.OL

Abstract

Enantioselective catalysis in moderate to excellent yields and ee's has been accomplished using a phosphaalkene-based ligand system. Specifically, the palladium-catalyzed allylic alkylation of 1,3-diphenyl-2-propenyl acetate using a chiral P(sp(2)),N(sp(2)) ligand proceeds with a variety of malonate nucleophiles in 73-95% yield (79-92% ee).

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Publisher Full Text (DOI)

Authors+Show Affiliations

Dugal-Tessier J
Department of Chemistry, 2036 Main Mall, University of British Columbia, Vancouver, B.C., Canada, V6T 1Z1.
Dake GR
No affiliation info available
Gates DP
No affiliation info available

MeSH

AlkenesAlkylationAllyl CompoundsCatalysisLigandsModels, MolecularMolecular StructureOxazolesPalladiumPhosphatesStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

20863121

Citation

Dugal-Tessier, Julien, et al. "Chiral Phosphaalkene-oxazoline Ligands for the Palladium-catalyzed Asymmetric Allylic Alkylation." Organic Letters, vol. 12, no. 20, 2010, pp. 4667-9.
Dugal-Tessier J, Dake GR, Gates DP. Chiral phosphaalkene-oxazoline ligands for the palladium-catalyzed asymmetric allylic alkylation. Org Lett. 2010;12(20):4667-9.
Dugal-Tessier, J., Dake, G. R., & Gates, D. P. (2010). Chiral phosphaalkene-oxazoline ligands for the palladium-catalyzed asymmetric allylic alkylation. Organic Letters, 12(20), 4667-9. https://doi.org/10.1021/ol1020652
Dugal-Tessier J, Dake GR, Gates DP. Chiral Phosphaalkene-oxazoline Ligands for the Palladium-catalyzed Asymmetric Allylic Alkylation. Org Lett. 2010 Oct 15;12(20):4667-9. PubMed PMID: 20863121.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Chiral phosphaalkene-oxazoline ligands for the palladium-catalyzed asymmetric allylic alkylation. AU - Dugal-Tessier,Julien, AU - Dake,Gregory R, AU - Gates,Derek P, PY - 2010/9/25/entrez PY - 2010/9/25/pubmed PY - 2011/1/22/medline SP - 4667 EP - 9 JF - Organic letters JO - Org Lett VL - 12 IS - 20 N2 - Enantioselective catalysis in moderate to excellent yields and ee's has been accomplished using a phosphaalkene-based ligand system. Specifically, the palladium-catalyzed allylic alkylation of 1,3-diphenyl-2-propenyl acetate using a chiral P(sp(2)),N(sp(2)) ligand proceeds with a variety of malonate nucleophiles in 73-95% yield (79-92% ee). SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/20863121/Chiral_phosphaalkene_oxazoline_ligands_for_the_palladium_catalyzed_asymmetric_allylic_alkylation_ L2 - https://doi.org/10.1021/ol1020652 DB - PRIME DP - Unbound Medicine ER -