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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
; and
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 (ACS)
external identifiers
  • scopus:0343994156
ISSN
1520-6904
DOI
10.1021/jo9601167
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
c0e8bff6-792a-4222-b0a9-6d5b35c7a59d (old id 31494)
date added to LUP
2016-04-01 11:37:23
date last changed
2022-01-26 07:48:39
@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 (ACS)}},
  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}},
  doi          = {{10.1021/jo9601167}},
  volume       = {{61}},
  year         = {{1996}},
}