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Is a hydrogen bonded carbene an intermediate in the organoaluminum-induced ring opening of pyranosides?

Olsson, Roger LU orcid ; Berg, Ulf LU and Frejd, Torbjörn LU (1997) In Tetrahedron Letters 38(32). p.5701-5704
Abstract

Semiempirical and ab initio quantum chemical computations indicate that the intermediate formed prior to the selectivity-determining methyl transfer step in the reaction between glycosides and trimethylaluminum is a strongly hydrogen-bended equilibrium OH...C = O-H...C, which is proposed to be an important selectivity promoting factor in the alkyl transfer reaction.

Please use this url to cite or link to this publication:
author
; and
organization
publishing date
type
Contribution to journal
publication status
published
in
Tetrahedron Letters
volume
38
issue
32
pages
4 pages
publisher
Elsevier
external identifiers
  • scopus:0030843287
ISSN
0040-4039
DOI
10.1016/S0040-4039(97)01250-1
language
English
LU publication?
yes
id
de62cb7e-a5ab-4a33-88d1-a6aed2ae2f01
date added to LUP
2019-10-02 10:49:43
date last changed
2025-10-14 11:37:15
@article{de62cb7e-a5ab-4a33-88d1-a6aed2ae2f01,
  abstract     = {{<p>Semiempirical and ab initio quantum chemical computations indicate that the intermediate formed prior to the selectivity-determining methyl transfer step in the reaction between glycosides and trimethylaluminum is a strongly hydrogen-bended equilibrium OH...C = O-H...C, which is proposed to be an important selectivity promoting factor in the alkyl transfer reaction.</p>}},
  author       = {{Olsson, Roger and Berg, Ulf and Frejd, Torbjörn}},
  issn         = {{0040-4039}},
  language     = {{eng}},
  month        = {{08}},
  number       = {{32}},
  pages        = {{5701--5704}},
  publisher    = {{Elsevier}},
  series       = {{Tetrahedron Letters}},
  title        = {{Is a hydrogen bonded carbene an intermediate in the organoaluminum-induced ring opening of pyranosides?}},
  url          = {{http://dx.doi.org/10.1016/S0040-4039(97)01250-1}},
  doi          = {{10.1016/S0040-4039(97)01250-1}},
  volume       = {{38}},
  year         = {{1997}},
}