Gold(I)-Catalysed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals

Carlos Palo Nieto; Abhijit Sau; Carmen Galan

doi:10.1021/jacs.7b08898

Gold(I)-Catalysed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals

Carlos Palo Nieto
, Abhijit Sau
, Carmen Galan

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

99 Citations (Scopus)

372 Downloads (Pure)

Abstract

Au(I) in combination with AgOTf enables the unprecedented direct and a-stereoselective catalytic synthesis of deoxyglycosides from glycals. Mechanistic investigations suggest that the reaction proceeds via Au(I)-catalysed 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.

Original language	English
Pages (from-to)	14041-14044
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	40
Early online date	21 Sept 2017
DOIs	https://doi.org/10.1021/jacs.7b08898
Publication status	Published - 11 Oct 2017

Research Groups and Themes

Organic & Biological

Access to Document

10.1021/jacs.7b08898

Full-text PDF (accepted author manuscript)
This is the author accepted manuscript (AAM). The final published version (version of record) is available online via ACS at http://pubs.acs.org/doi/10.1021/jacs.7b08898 . Please refer to any applicable terms of use of the publisher.
Accepted author manuscript, 500 KB

Handle.net

Persistent link

3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research
Reworking of Novel tools for Glycoscience
Galan, M. C. (Principal Investigator)
31/03/12 → 30/08/17
Project: Research

Professor M C Galan
- M.C.Galanbristol.acuk
- School of Chemistry - Professor of Organic and Biological Chemistry
Person: Academic

Cite this

@article{be16a22908c042d5949bb247d282950b,

title = "Gold(I)-Catalysed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals",

abstract = "Au(I) in combination with AgOTf enables the unprecedented direct and a-stereoselective catalytic synthesis of deoxyglycosides from glycals. Mechanistic investigations suggest that the reaction proceeds via Au(I)-catalysed 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. ",

author = "\{Palo Nieto\}, Carlos and Abhijit Sau and Carmen Galan",

year = "2017",

month = oct,

day = "11",

doi = "10.1021/jacs.7b08898",

language = "English",

volume = "139",

pages = "14041--14044",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "40",

}

TY - JOUR

T1 - Gold(I)-Catalysed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals

AU - Palo Nieto, Carlos

AU - Sau, Abhijit

AU - Galan, Carmen

PY - 2017/10/11

Y1 - 2017/10/11

N2 - Au(I) in combination with AgOTf enables the unprecedented direct and a-stereoselective catalytic synthesis of deoxyglycosides from glycals. Mechanistic investigations suggest that the reaction proceeds via Au(I)-catalysed 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.

AB - Au(I) in combination with AgOTf enables the unprecedented direct and a-stereoselective catalytic synthesis of deoxyglycosides from glycals. Mechanistic investigations suggest that the reaction proceeds via Au(I)-catalysed 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.

U2 - 10.1021/jacs.7b08898

DO - 10.1021/jacs.7b08898

M3 - Article (Academic Journal)

C2 - 28934850

SN - 0002-7863

VL - 139

SP - 14041

EP - 14044

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 40

ER -

Gold(I)-Catalysed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals

Abstract

Research Groups and Themes

Access to Document

Handle.net

Fingerprint

Projects

3-month Core Capability for Chemistry Research

Reworking of Novel tools for Glycoscience

Profiles

Professor M C Galan

Cite this