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

Summary, in English

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: Fredrik Almqvist; Niklas Ekman; Torbjörn Frejd
• Department/s: Centre for Analysis and Synthesis
• Publishing year: 1996
• Language: English
• Pages: 3794-3798
• Publication/Series: Journal of Organic Chemistry
• Volume: 61
• Issue: 11
• Links: http://dx.doi.org/10.1021/jo9601167
• Document type: Journal article
• Publisher: The American Chemical Society (ACS)
• Topic: Organic Chemistry
• Status: Published
• ISBN/ISSN/Other: ISSN: 1520-6904