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
(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).
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/31494
- author
- Almqvist, Fredrik ; Ekman, Niklas and Frejd, Torbjörn LU
- organization
- publishing date
- 1996
- 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}}, }