Tags

Type your tag names separated by a space and hit enter

Copper Reactivity Can Be Tuned to Catalyze the Stereoselective Synthesis of 2-Deoxyglycosides from Glycals.
Org Lett. 2020 03 06; 22(5):1991-1996.OL

Abstract

We demonstrate that tuning the reactivity of Cu by the choice of oxidation state and counterion leads to the activation of both "armed" and "disarmed" type glycals toward direct glycosylation leading to the α-stereoselective synthesis of deoxyglycosides in good to excellent yields. Mechanistic studies show that CuI is essential for effective catalysis and stereocontrol and that the reaction proceeds through dual activation of both the enol ether as well as the OH nucleophile.

Authors+Show Affiliations

School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 3TS, United Kingdom.School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 3TS, United Kingdom.School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 3TS, United Kingdom.Laboratoire des biomolécules (LBM), Sorbonne Université - Ecole Normale Supérieure - CNRS, 24 rue Lhomond, 75005 Paris, France.Laboratoire des biomolécules (LBM), Sorbonne Université - Ecole Normale Supérieure - CNRS, 24 rue Lhomond, 75005 Paris, France.School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, Av do Café s/n, Monte Alegre CEP 14040-903, Brazil.School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, Av do Café s/n, Monte Alegre CEP 14040-903, Brazil.Laboratoire des biomolécules (LBM), Sorbonne Université - Ecole Normale Supérieure - CNRS, 24 rue Lhomond, 75005 Paris, France.School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 3TS, United Kingdom.

Pub Type(s)

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

Language

eng

PubMed ID

32073274

Citation

Palo-Nieto, Carlos, et al. "Copper Reactivity Can Be Tuned to Catalyze the Stereoselective Synthesis of 2-Deoxyglycosides From Glycals." Organic Letters, vol. 22, no. 5, 2020, pp. 1991-1996.
Palo-Nieto C, Sau A, Jeanneret R, et al. Copper Reactivity Can Be Tuned to Catalyze the Stereoselective Synthesis of 2-Deoxyglycosides from Glycals. Org Lett. 2020;22(5):1991-1996.
Palo-Nieto, C., Sau, A., Jeanneret, R., Payard, P. A., Salamé, A., Martins-Teixeira, M. B., Carvalho, I., Grimaud, L., & Galan, M. C. (2020). Copper Reactivity Can Be Tuned to Catalyze the Stereoselective Synthesis of 2-Deoxyglycosides from Glycals. Organic Letters, 22(5), 1991-1996. https://doi.org/10.1021/acs.orglett.9b04525
Palo-Nieto C, et al. Copper Reactivity Can Be Tuned to Catalyze the Stereoselective Synthesis of 2-Deoxyglycosides From Glycals. Org Lett. 2020 03 6;22(5):1991-1996. PubMed PMID: 32073274.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Copper Reactivity Can Be Tuned to Catalyze the Stereoselective Synthesis of 2-Deoxyglycosides from Glycals. AU - Palo-Nieto,Carlos, AU - Sau,Abhijit, AU - Jeanneret,Robin, AU - Payard,Pierre-Adrien, AU - Salamé,Aude, AU - Martins-Teixeira,Maristela Braga, AU - Carvalho,Ivone, AU - Grimaud,Laurence, AU - Galan,M Carmen, Y1 - 2020/02/19/ PY - 2020/2/20/pubmed PY - 2020/2/20/medline PY - 2020/2/20/entrez SP - 1991 EP - 1996 JF - Organic letters JO - Org. Lett. VL - 22 IS - 5 N2 - We demonstrate that tuning the reactivity of Cu by the choice of oxidation state and counterion leads to the activation of both "armed" and "disarmed" type glycals toward direct glycosylation leading to the α-stereoselective synthesis of deoxyglycosides in good to excellent yields. Mechanistic studies show that CuI is essential for effective catalysis and stereocontrol and that the reaction proceeds through dual activation of both the enol ether as well as the OH nucleophile. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/32073274/Copper_Reactivity_Can_Be_Tuned_to_Catalyze_the_Stereoselective_Synthesis_of_2_Deoxyglycosides_from_Glycals_ L2 - https://doi.org/10.1021/acs.orglett.9b04525 DB - PRIME DP - Unbound Medicine ER -
Try the Free App:
Prime PubMed app for iOS iPhone iPad
Prime PubMed app for Android
Prime PubMed is provided
free to individuals by:
Unbound Medicine.