Palladium-catalysed direct stereoselective synthesis of deoxyglycosides from glycals

Abhijit Sau; Ryan Williams; Carlos Palo Nieto; Antonio Franconetti Garcia; Sandra Medina Villar; Carmen Galan

doi:10.1002/anie.201612071

Palladium-catalysed direct stereoselective synthesis of deoxyglycosides from glycals

Abhijit Sau, Ryan Williams, Carlos Palo Nieto, Antonio Franconetti Garcia, Sandra Medina Villar, Carmen Galan

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

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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 exemplified with a wide range of glycal donors and acceptors, including substrates bearing alkene functionalities.

Original language	English
Pages (from-to)	3640–3644
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	13
Early online date	17 Feb 2017
DOIs	https://doi.org/10.1002/anie.201612071
Publication status	Published - 20 Mar 2017

Keywords

acetals
asymmetric catalysis
deoxyglycosides
glycosylation
palladium

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10.1002/anie.201612071

Full-text PDF (accepted author manuscript)
This is the author accepted manuscript (AAM). The final published version (version of record) is available online via Wiley at http://onlinelibrary.wiley.com/doi/10.1002/anie.201612071/full . Please refer to any applicable terms of use of the publisher.
Accepted author manuscript, 1.07 MB

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Catalytic stereoselective synthesis of glycosides
Galan, M. C. (Principal Investigator)
1/07/13 → 1/07/15
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

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title = "Palladium-catalysed direct stereoselective synthesis of deoxyglycosides from glycals",

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 exemplified with a wide range of glycal donors and acceptors, including substrates bearing alkene functionalities.",

keywords = "acetals, asymmetric catalysis, deoxyglycosides, glycosylation, palladium",

author = "Abhijit Sau and Ryan Williams and {Palo Nieto}, Carlos and {Franconetti Garcia}, Antonio and {Medina Villar}, Sandra and Carmen Galan",

year = "2017",

month = mar,

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doi = "10.1002/anie.201612071",

language = "English",

volume = "56",

pages = "3640–3644",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "Wiley-VCH Verlag",

number = "13",

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TY - JOUR

T1 - Palladium-catalysed direct stereoselective synthesis of deoxyglycosides from glycals

AU - Sau, Abhijit

AU - Williams, Ryan

AU - Palo Nieto, Carlos

AU - Franconetti Garcia, Antonio

AU - Medina Villar, Sandra

AU - Galan, Carmen

PY - 2017/3/20

Y1 - 2017/3/20

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 exemplified with a wide range of glycal donors and acceptors, including substrates bearing alkene functionalities.

AB - 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 exemplified with a wide range of glycal donors and acceptors, including substrates bearing alkene functionalities.

KW - acetals

KW - asymmetric catalysis

KW - deoxyglycosides

KW - glycosylation

KW - palladium

U2 - 10.1002/anie.201612071

DO - 10.1002/anie.201612071

M3 - Article (Academic Journal)

C2 - 28211228

SN - 1433-7851

VL - 56

SP - 3640

EP - 3644

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 13

ER -

Palladium-catalysed direct stereoselective synthesis of deoxyglycosides from glycals

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Keywords

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Projects

Catalytic stereoselective synthesis of glycosides

Reworking of Novel tools for Glycoscience

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Professor M C Galan

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