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Palladium-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals.
Angew Chem Int Ed Engl. 2017 03 20; 56(13):3640-3644.AC

Abstract

Palladium(II) in combination with a monodentate phosphine ligand enables the unprecedented direct and α-stereoselective catalytic synthesis of deoxyglycosides from glycals. Initial mechanistic studies suggest that in the presence of N-phenyl-2-(di-tert-butylphosphino)pyrrole as the ligand, the reaction proceeds via an alkoxy palladium intermediate that increases the proton acidity and oxygen nucleophilicity of the alcohol. The method is demonstrated with a wide range of glycal donors and acceptors, including substrates bearing alkene functionalities.

Authors+Show Affiliations

School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.

Pub Type(s)

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

Language

eng

PubMed ID

28211228

Citation

Sau, Abhijit, et al. "Palladium-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides From Glycals." Angewandte Chemie (International Ed. in English), vol. 56, no. 13, 2017, pp. 3640-3644.
Sau A, Williams R, Palo-Nieto C, et al. Palladium-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals. Angew Chem Int Ed Engl. 2017;56(13):3640-3644.
Sau, A., Williams, R., Palo-Nieto, C., Franconetti, A., Medina, S., & Galan, M. C. (2017). Palladium-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals. Angewandte Chemie (International Ed. in English), 56(13), 3640-3644. https://doi.org/10.1002/anie.201612071
Sau A, et al. Palladium-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides From Glycals. Angew Chem Int Ed Engl. 2017 03 20;56(13):3640-3644. PubMed PMID: 28211228.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals. AU - Sau,Abhijit, AU - Williams,Ryan, AU - Palo-Nieto,Carlos, AU - Franconetti,Antonio, AU - Medina,Sandra, AU - Galan,M Carmen, Y1 - 2017/02/17/ PY - 2016/12/12/received PY - 2017/01/26/revised PY - 2017/2/18/pubmed PY - 2017/2/18/medline PY - 2017/2/18/entrez KW - acetals KW - asymmetric catalysis KW - deoxyglycosides KW - glycosylation KW - palladium SP - 3640 EP - 3644 JF - Angewandte Chemie (International ed. in English) JO - Angew. Chem. Int. Ed. Engl. VL - 56 IS - 13 N2 - Palladium(II) in combination with a monodentate phosphine ligand enables the unprecedented direct and α-stereoselective catalytic synthesis of deoxyglycosides from glycals. Initial mechanistic studies suggest that in the presence of N-phenyl-2-(di-tert-butylphosphino)pyrrole as the ligand, the reaction proceeds via an alkoxy palladium intermediate that increases the proton acidity and oxygen nucleophilicity of the alcohol. The method is demonstrated with a wide range of glycal donors and acceptors, including substrates bearing alkene functionalities. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/28211228/Palladium_Catalyzed_Direct_Stereoselective_Synthesis_of_Deoxyglycosides_from_Glycals_ DB - PRIME DP - Unbound Medicine ER -
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