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Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides.
J Org Chem. 2017 01 06; 82(1):407-414.JO

Abstract

A practical approach for the α-stereoselective synthesis of deoxyglycosides using cooperative Brønsted acid-type organocatalysis has been developed. The method is tolerant of a wide range of glycoside donors and acceptors, and its versatility is exemplified in the one-pot synthesis of a trisaccharide. Mechanistic studies suggest that thiourea-induced acid amplification of the chiral acid via H-bonding is key for the enhancement in reaction rate and yield, while stereocontrol is dependent on the chirality of the acid.

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.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

28004941

Citation

Palo-Nieto, Carlos, et al. "Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides." The Journal of Organic Chemistry, vol. 82, no. 1, 2017, pp. 407-414.
Palo-Nieto C, Sau A, Williams R, et al. Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides. J Org Chem. 2017;82(1):407-414.
Palo-Nieto, C., Sau, A., Williams, R., & Galan, M. C. (2017). Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides. The Journal of Organic Chemistry, 82(1), 407-414. https://doi.org/10.1021/acs.joc.6b02498
Palo-Nieto C, et al. Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides. J Org Chem. 2017 01 6;82(1):407-414. PubMed PMID: 28004941.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides. AU - Palo-Nieto,Carlos, AU - Sau,Abhijit, AU - Williams,Ryan, AU - Galan,M Carmen, Y1 - 2016/12/22/ PY - 2016/12/23/pubmed PY - 2016/12/23/medline PY - 2016/12/23/entrez SP - 407 EP - 414 JF - The Journal of organic chemistry JO - J. Org. Chem. VL - 82 IS - 1 N2 - A practical approach for the α-stereoselective synthesis of deoxyglycosides using cooperative Brønsted acid-type organocatalysis has been developed. The method is tolerant of a wide range of glycoside donors and acceptors, and its versatility is exemplified in the one-pot synthesis of a trisaccharide. Mechanistic studies suggest that thiourea-induced acid amplification of the chiral acid via H-bonding is key for the enhancement in reaction rate and yield, while stereocontrol is dependent on the chirality of the acid. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/28004941/Cooperative_Brønsted_Acid_Type_Organocatalysis_for_the_Stereoselective_Synthesis_of_Deoxyglycosides_ L2 - https://dx.doi.org/10.1021/acs.joc.6b02498 DB - PRIME DP - Unbound Medicine ER -
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