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Endocyclic cleavage of glycosides. VI. Substituent effects of the alkylative endocyclic cleavage of glycosides

Olsson, Roger LU ; Berg, Ulf LU and Frejd, Torbjörn LU (1998) In Tetrahedron 54(15). p.3935-3954
Abstract


A number of pentopyranoside derivatives were treated with Me
3
Al in order to investigate the influence of structural parameters on the methyl group transfer in the endocyclic alkylative cleavage reaction of these substrates. A cyclic CH ··· O hydrogen bonded model is suggested as an intermediate, which is used to explain the stereoselectivities for different substrates. In several, cases the diastereoselectivities were better than 9:1.

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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Tetrahedron
volume
54
issue
15
pages
3935 - 3954
publisher
Elsevier
external identifiers
  • scopus:0032499014
ISSN
0040-4020
DOI
10.1016/S0040-4020(98)00120-3
language
English
LU publication?
yes
id
d3e707a7-e3e1-49d1-a153-02f59d60fa99
date added to LUP
2019-10-02 10:52:16
date last changed
2020-01-13 02:26:18
@article{d3e707a7-e3e1-49d1-a153-02f59d60fa99,
  abstract     = {<p><br>
                            A number of pentopyranoside derivatives were treated with Me<br>
                            <sub>3</sub><br>
                            Al in order to investigate the influence of structural parameters on the methyl group transfer in the endocyclic alkylative cleavage reaction of these substrates. A cyclic CH ··· O hydrogen bonded model is suggested as an intermediate, which is used to explain the stereoselectivities for different substrates. In several, cases the diastereoselectivities were better than 9:1.<br>
                        </p>},
  author       = {Olsson, Roger and Berg, Ulf and Frejd, Torbjörn},
  issn         = {0040-4020},
  language     = {eng},
  month        = {04},
  number       = {15},
  pages        = {3935--3954},
  publisher    = {Elsevier},
  series       = {Tetrahedron},
  title        = {Endocyclic cleavage of glycosides. VI. Substituent effects of the alkylative endocyclic cleavage of glycosides},
  url          = {http://dx.doi.org/10.1016/S0040-4020(98)00120-3},
  doi          = {10.1016/S0040-4020(98)00120-3},
  volume       = {54},
  year         = {1998},
}