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Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals.
J Am Chem Soc. 2017 10 11; 139(40):14041-14044.JA

Abstract

Au(I) in combination with AgOTf enables the unprecedented direct and α-stereoselective catalytic synthesis of deoxyglycosides from glycals. Mechanistic investigations suggest that the reaction proceeds via Au(I)-catalyzed hydrofunctionalization of the enol ether glycoside. The room temperature reaction is high yielding and amenable to a wide range of glycal donors and OH nucleophiles.

Authors+Show Affiliations

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

Pub Type(s)

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

Language

eng

PubMed ID

28934850

Citation

Palo-Nieto, Carlos, et al. "Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides From Glycals." Journal of the American Chemical Society, vol. 139, no. 40, 2017, pp. 14041-14044.
Palo-Nieto C, Sau A, Galan MC. Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals. J Am Chem Soc. 2017;139(40):14041-14044.
Palo-Nieto, C., Sau, A., & Galan, M. C. (2017). Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals. Journal of the American Chemical Society, 139(40), 14041-14044. https://doi.org/10.1021/jacs.7b08898
Palo-Nieto C, Sau A, Galan MC. Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides From Glycals. J Am Chem Soc. 2017 10 11;139(40):14041-14044. PubMed PMID: 28934850.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals. AU - Palo-Nieto,Carlos, AU - Sau,Abhijit, AU - Galan,M Carmen, Y1 - 2017/09/28/ PY - 2017/9/25/pubmed PY - 2018/6/12/medline PY - 2017/9/23/entrez SP - 14041 EP - 14044 JF - Journal of the American Chemical Society JO - J. Am. Chem. Soc. VL - 139 IS - 40 N2 - Au(I) in combination with AgOTf enables the unprecedented direct and α-stereoselective catalytic synthesis of deoxyglycosides from glycals. Mechanistic investigations suggest that the reaction proceeds via Au(I)-catalyzed hydrofunctionalization of the enol ether glycoside. The room temperature reaction is high yielding and amenable to a wide range of glycal donors and OH nucleophiles. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/28934850/Gold_I__Catalyzed_Direct_Stereoselective_Synthesis_of_Deoxyglycosides_from_Glycals_ L2 - https://dx.doi.org/10.1021/jacs.7b08898 DB - PRIME DP - Unbound Medicine ER -