A new route to exo-glycals using the Ramberg-Bäcklund rearrangement

Frank K. Griffin; Duncan E. Paterson; Paul V. Murphy; Richard J.K. Taylor

doi:10.1002/1099-0690(200204)2002:7<1305::AID-EJOC1305>3.0.CO;2-0

A new route to exo-glycals using the Ramberg-Bäcklund rearrangement

Frank K. Griffin
, Duncan E. Paterson
, Paul V. Murphy
, Richard J.K. Taylor

University of York

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

53 Citations (Scopus)

Abstract

A new route to exo-glycals 4 is described in which glycosyl sulfones 3 are subjected to the Meyers variant of the Ramberg-Bäcklund rearrangement. The conversion of sulfones derived from glucose, galactose, mannose, cellobiose, and ribose into di-, tri-, and tetra-substituted alkenes is reported. Preliminary mechanistic studies of this process are also described.

Original language	English
Pages (from-to)	1305-1322
Number of pages	18
Journal	European Journal of Organic Chemistry
Issue number	7
DOIs	https://doi.org/10.1002/1099-0690(200204)2002:7<1305::AID-EJOC1305>3.0.CO;2-0
Publication status	Published - 2002
Externally published	Yes

Keywords

Carbohydrates
Enol ethers
Rearrangements
Sulfones

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10.1002/1099-0690(200204)2002:7<1305::AID-EJOC1305>3.0.CO;2-0

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title = "A new route to exo-glycals using the Ramberg-B{\"a}cklund rearrangement",

abstract = "A new route to exo-glycals 4 is described in which glycosyl sulfones 3 are subjected to the Meyers variant of the Ramberg-B{\"a}cklund rearrangement. The conversion of sulfones derived from glucose, galactose, mannose, cellobiose, and ribose into di-, tri-, and tetra-substituted alkenes is reported. Preliminary mechanistic studies of this process are also described.",

keywords = "Carbohydrates, Enol ethers, Rearrangements, Sulfones",

author = "Griffin, \{Frank K.\} and Paterson, \{Duncan E.\} and Murphy, \{Paul V.\} and Taylor, \{Richard J.K.\}",

year = "2002",

doi = "10.1002/1099-0690(200204)2002:7<1305::AID-EJOC1305>3.0.CO;2-0",

language = "English",

pages = "1305--1322",

journal = "European Journal of Organic Chemistry",

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publisher = "Wiley-VCH Verlag",

number = "7",

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TY - JOUR

T1 - A new route to exo-glycals using the Ramberg-Bäcklund rearrangement

AU - Griffin, Frank K.

AU - Paterson, Duncan E.

AU - Murphy, Paul V.

AU - Taylor, Richard J.K.

PY - 2002

Y1 - 2002

N2 - A new route to exo-glycals 4 is described in which glycosyl sulfones 3 are subjected to the Meyers variant of the Ramberg-Bäcklund rearrangement. The conversion of sulfones derived from glucose, galactose, mannose, cellobiose, and ribose into di-, tri-, and tetra-substituted alkenes is reported. Preliminary mechanistic studies of this process are also described.

AB - A new route to exo-glycals 4 is described in which glycosyl sulfones 3 are subjected to the Meyers variant of the Ramberg-Bäcklund rearrangement. The conversion of sulfones derived from glucose, galactose, mannose, cellobiose, and ribose into di-, tri-, and tetra-substituted alkenes is reported. Preliminary mechanistic studies of this process are also described.

KW - Carbohydrates

KW - Enol ethers

KW - Rearrangements

KW - Sulfones

UR - https://www.scopus.com/pages/publications/0036218393

U2 - 10.1002/1099-0690(200204)2002:7<1305::AID-EJOC1305>3.0.CO;2-0

DO - 10.1002/1099-0690(200204)2002:7<1305::AID-EJOC1305>3.0.CO;2-0

M3 - Article

SN - 1434-193X

SP - 1305

EP - 1322

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 7

ER -

A new route to exo-glycals using the Ramberg-Bäcklund rearrangement

Abstract

Keywords

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