Reactivity of 1,2-cyclic sulfite xylosides towards nucleophiles

Nathalie Batoux; Christopher Hardacre; Marie E. Migaud; Kerry A. Ness; Sarah E. Norman

doi:10.1016/j.tet.2009.08.053

Reactivity of 1,2-cyclic sulfite xylosides towards nucleophiles

Nathalie Batoux, Christopher Hardacre, Marie E. Migaud, Kerry A. Ness, Sarah E. Norman

Queen's University Belfast

Research output: Contribution to journal › Article › peer-review

Abstract

1,2-Cyclic sulfite xylosides offer facile access to 1,2-oxazolines upon reaction with aromatic and alkyl nitriles under Lewis or Brönsted acid conditions. Additionally, hydrophobic ionic liquids facilitate acid-catalysed formations of such oxazolines and C- and O-linked xylosides, providing means to carry out fast reactions at room temperature, and this in yields comparable to reactions conducted in xylene at high temperature for extended reaction time.

Original language	English
Pages (from-to)	8858-8862
Number of pages	5
Journal	Tetrahedron
Volume	65
Issue number	43
DOIs	https://doi.org/10.1016/j.tet.2009.08.053
Publication status	Published - 24 Oct 2009

Keywords

C-, O-linked furanosides
C-nucleosides
Cyclic sulfites
Ionic liquids
Oxazoline

Access to Document

10.1016/j.tet.2009.08.053

Cite this

@article{6bc457638fe14f3ba70b465221cb4bb3,

title = "Reactivity of 1,2-cyclic sulfite xylosides towards nucleophiles",

abstract = "1,2-Cyclic sulfite xylosides offer facile access to 1,2-oxazolines upon reaction with aromatic and alkyl nitriles under Lewis or Br{\"o}nsted acid conditions. Additionally, hydrophobic ionic liquids facilitate acid-catalysed formations of such oxazolines and C- and O-linked xylosides, providing means to carry out fast reactions at room temperature, and this in yields comparable to reactions conducted in xylene at high temperature for extended reaction time.",

keywords = "C-, O-linked furanosides, C-nucleosides, Cyclic sulfites, Ionic liquids, Oxazoline",

author = "Nathalie Batoux and Christopher Hardacre and Migaud, {Marie E.} and Ness, {Kerry A.} and Norman, {Sarah E.}",

year = "2009",

month = oct,

day = "24",

doi = "10.1016/j.tet.2009.08.053",

language = "English",

volume = "65",

pages = "8858--8862",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier BV",

number = "43",

}

TY - JOUR

T1 - Reactivity of 1,2-cyclic sulfite xylosides towards nucleophiles

AU - Batoux, Nathalie

AU - Hardacre, Christopher

AU - Migaud, Marie E.

AU - Ness, Kerry A.

AU - Norman, Sarah E.

PY - 2009/10/24

Y1 - 2009/10/24

N2 - 1,2-Cyclic sulfite xylosides offer facile access to 1,2-oxazolines upon reaction with aromatic and alkyl nitriles under Lewis or Brönsted acid conditions. Additionally, hydrophobic ionic liquids facilitate acid-catalysed formations of such oxazolines and C- and O-linked xylosides, providing means to carry out fast reactions at room temperature, and this in yields comparable to reactions conducted in xylene at high temperature for extended reaction time.

AB - 1,2-Cyclic sulfite xylosides offer facile access to 1,2-oxazolines upon reaction with aromatic and alkyl nitriles under Lewis or Brönsted acid conditions. Additionally, hydrophobic ionic liquids facilitate acid-catalysed formations of such oxazolines and C- and O-linked xylosides, providing means to carry out fast reactions at room temperature, and this in yields comparable to reactions conducted in xylene at high temperature for extended reaction time.

KW - C-, O-linked furanosides

KW - C-nucleosides

KW - Cyclic sulfites

KW - Ionic liquids

KW - Oxazoline

UR - http://www.scopus.com/inward/record.url?scp=70349159507&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2009.08.053

DO - 10.1016/j.tet.2009.08.053

M3 - Article

AN - SCOPUS:70349159507

VL - 65

SP - 8858

EP - 8862

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 43

ER -

Reactivity of 1,2-cyclic sulfite xylosides towards nucleophiles

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this