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Enantioselective synthesis of bridgehead hydroxyl bicyclo[2.2.2]octane derivatives via asymmetric allylindation

Thornqvist, Viveca LU ; Manner, Sophie LU and Frejd, Torbjörn LU (2006) In Tetrahedron: Asymmetry 17(3). p.410-415
Abstract
A recent new strategy for the transformation of mono-dioxolane protected 1,3-cyclohexadione into bridgehead hydroxyl bicyclo[2.2.2]octane derivatives, based on allylindation followed by ozonolysis and intramolecular aldol addition, was modified to include asymmetric allylindation. This enabled the first enantioselective synthesis of (1R,4R,6S)-endo-4-(tert-butyl-dimethyl-silyloxy)-6-hydroxy-bicyclo[2.2.2 ]octan-2-one and (1S,4S,6R)-endo-4-(tert-butyl-dimethyl-silyloxy)-6-hydroxy-bicyclo[2.2.2 ]octan-2-one in high enantiomeric excess. Issues concerning the non-reproducibility of the asymmetric allylindation were also addressed. (c) 2006 Elsevier Ltd. All rights reserved.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Tetrahedron: Asymmetry
volume
17
issue
3
pages
410 - 415
publisher
Elsevier
external identifiers
  • wos:000236256700014
  • scopus:33644679573
ISSN
0957-4166
DOI
10.1016/j.tetasy.2005.12.026
language
English
LU publication?
yes
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
id
16745654-fe0e-42f1-8472-9df0468adfbf (old id 414980)
date added to LUP
2016-04-01 15:52:22
date last changed
2020-01-12 18:48:57
@article{16745654-fe0e-42f1-8472-9df0468adfbf,
  abstract     = {A recent new strategy for the transformation of mono-dioxolane protected 1,3-cyclohexadione into bridgehead hydroxyl bicyclo[2.2.2]octane derivatives, based on allylindation followed by ozonolysis and intramolecular aldol addition, was modified to include asymmetric allylindation. This enabled the first enantioselective synthesis of (1R,4R,6S)-endo-4-(tert-butyl-dimethyl-silyloxy)-6-hydroxy-bicyclo[2.2.2 ]octan-2-one and (1S,4S,6R)-endo-4-(tert-butyl-dimethyl-silyloxy)-6-hydroxy-bicyclo[2.2.2 ]octan-2-one in high enantiomeric excess. Issues concerning the non-reproducibility of the asymmetric allylindation were also addressed. (c) 2006 Elsevier Ltd. All rights reserved.},
  author       = {Thornqvist, Viveca and Manner, Sophie and Frejd, Torbjörn},
  issn         = {0957-4166},
  language     = {eng},
  number       = {3},
  pages        = {410--415},
  publisher    = {Elsevier},
  series       = {Tetrahedron: Asymmetry},
  title        = {Enantioselective synthesis of bridgehead hydroxyl bicyclo[2.2.2]octane derivatives via asymmetric allylindation},
  url          = {http://dx.doi.org/10.1016/j.tetasy.2005.12.026},
  doi          = {10.1016/j.tetasy.2005.12.026},
  volume       = {17},
  year         = {2006},
}