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A new class of substituted aryl bis(oxazoline) ligands for highly enantioselective copper-catalyzed asymmetric aldol addition of dienolsilane to pyruvate and glyoxylate esters.
Org Lett. 2004 Oct 28; 6(22):4097-9.OL

Abstract

[reaction: see text] A new class of bis(oxazoline) ligands are introduced that feature o-alkoxyaryl substituents and provide the highest enantioselectivities yet reported for the copper-catalyzed asymmetric dienosilane aldol addition to pyruvate and glyoxylate esters. Enantioselectivities up to 98% ee (before recrystallization) and isolated yields up to 91% were observed. Additionally, chloride counterions were found to be superior to triflate for this reaction.

Authors+Show Affiliations

Le JC
The Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, USA.
Pagenkopf BL
No affiliation info available

MeSH

AldehydesCatalysisChloridesCopperEstersGlyoxylatesHydrocarbons, AromaticLigandsMesylatesMolecular StructureOxazolesPyruvatesSilanesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

15496108

Citation

Le, Julie Cong-Dung, and Brian L. Pagenkopf. "A New Class of Substituted Aryl Bis(oxazoline) Ligands for Highly Enantioselective Copper-catalyzed Asymmetric Aldol Addition of Dienolsilane to Pyruvate and Glyoxylate Esters." Organic Letters, vol. 6, no. 22, 2004, pp. 4097-9.
Le JC, Pagenkopf BL. A new class of substituted aryl bis(oxazoline) ligands for highly enantioselective copper-catalyzed asymmetric aldol addition of dienolsilane to pyruvate and glyoxylate esters. Org Lett. 2004;6(22):4097-9.
Le, J. C., & Pagenkopf, B. L. (2004). A new class of substituted aryl bis(oxazoline) ligands for highly enantioselective copper-catalyzed asymmetric aldol addition of dienolsilane to pyruvate and glyoxylate esters. Organic Letters, 6(22), 4097-9.
Le JC, Pagenkopf BL. A New Class of Substituted Aryl Bis(oxazoline) Ligands for Highly Enantioselective Copper-catalyzed Asymmetric Aldol Addition of Dienolsilane to Pyruvate and Glyoxylate Esters. Org Lett. 2004 Oct 28;6(22):4097-9. PubMed PMID: 15496108.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A new class of substituted aryl bis(oxazoline) ligands for highly enantioselective copper-catalyzed asymmetric aldol addition of dienolsilane to pyruvate and glyoxylate esters. AU - Le,Julie Cong-Dung, AU - Pagenkopf,Brian L, PY - 2004/10/22/pubmed PY - 2005/8/2/medline PY - 2004/10/22/entrez SP - 4097 EP - 9 JF - Organic letters JO - Org Lett VL - 6 IS - 22 N2 - [reaction: see text] A new class of bis(oxazoline) ligands are introduced that feature o-alkoxyaryl substituents and provide the highest enantioselectivities yet reported for the copper-catalyzed asymmetric dienosilane aldol addition to pyruvate and glyoxylate esters. Enantioselectivities up to 98% ee (before recrystallization) and isolated yields up to 91% were observed. Additionally, chloride counterions were found to be superior to triflate for this reaction. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15496108/A_new_class_of_substituted_aryl_bis_oxazoline__ligands_for_highly_enantioselective_copper_catalyzed_asymmetric_aldol_addition_of_dienolsilane_to_pyruvate_and_glyoxylate_esters_ DB - PRIME DP - Unbound Medicine ER -