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Synthesis of Optically Active endo, endo Bicyclo[2.2.2]octane-2,5- diol, Bicyclo[2.2.2]octan-2,5-dione and Related Compounds

Almqvist, Fredrik; Ekman, Niklas and Frejd, Torbjörn LU (1996) In Journal of Organic Chemistry 61(11). p.3794-3798
Abstract
Optically active C-2-symmetric (1S,2S,4S,5S)-bicyclo[2.2.2]octane-2,5-diol ((+)-12; 98% ee) and several selectivity protected optically active intermediates useful for synthetic transformations were synthesized via a 1,2-carbonyl transposition route starting from the easily available optically active (1R,4S,6S)-6-hydroxybicyclo[2.2.2]octan-2-one ((-)-2). The synthetic route also allowed the preparation of optically active (1S,4S)-bicyclo[2.2.2]octane-2,5-dione ((+)-14; 98% ee).
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Organic Chemistry
volume
61
issue
11
pages
3794 - 3798
publisher
The American Chemical Society
ISSN
1520-6904
DOI
10.1021/jo9601167
language
English
LU publication?
yes
id
c0e8bff6-792a-4222-b0a9-6d5b35c7a59d (old id 31494)
date added to LUP
2007-06-19 14:27:13
date last changed
2016-04-15 18:41:36
@article{c0e8bff6-792a-4222-b0a9-6d5b35c7a59d,
  abstract     = {Optically active C-2-symmetric (1S,2S,4S,5S)-bicyclo[2.2.2]octane-2,5-diol ((+)-12; 98% ee) and several selectivity protected optically active intermediates useful for synthetic transformations were synthesized via a 1,2-carbonyl transposition route starting from the easily available optically active (1R,4S,6S)-6-hydroxybicyclo[2.2.2]octan-2-one ((-)-2). The synthetic route also allowed the preparation of optically active (1S,4S)-bicyclo[2.2.2]octane-2,5-dione ((+)-14; 98% ee).},
  author       = {Almqvist, Fredrik and Ekman, Niklas and Frejd, Torbjörn},
  issn         = {1520-6904},
  language     = {eng},
  number       = {11},
  pages        = {3794--3798},
  publisher    = {The American Chemical Society},
  series       = {Journal of Organic Chemistry},
  title        = {Synthesis of Optically Active endo, endo Bicyclo[2.2.2]octane-2,5- diol, Bicyclo[2.2.2]octan-2,5-dione and Related Compounds},
  url          = {http://dx.doi.org/10.1021/jo9601167},
  volume       = {61},
  year         = {1996},
}