Endocyclic cleavage of glycosides. VI. Substituent effects of the alkylative endocyclic cleavage of glycosides
(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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https://lup.lub.lu.se/record/d3e707a7-e3e1-49d1-a153-02f59d60fa99
- author
- Olsson, Roger LU ; Berg, Ulf LU and Frejd, Torbjörn LU
- organization
- publishing date
- 1998-04-09
- 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
- 2022-02-01 01:07:44
@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}}, }