Enantioselective synthesis of bridgehead hydroxyl bicyclo[2.2.2]octane derivatives via asymmetric allylindation
(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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/414980
- author
- Thornqvist, Viveca LU ; Manner, Sophie LU and Frejd, Torbjörn LU
- organization
- publishing date
- 2006
- 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
- 2022-03-14 20:31:53
@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}}, }