1351983-76-0Relevant academic research and scientific papers
PREPARATION OF BICYCLO[2.2.2]OCTAN-2-ONE COMPOUNDS
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Paragraph 0149; 0151; 0152, (2015/03/13)
The present invention relates to a new process for the preparation of 6-hydroxy-5-arylbicyclo[2.2.2]octan-2-one compounds of the formula (II); which may subsequently be further transformed to compounds of the formula (I): The present invention further relates to novel compounds as such, which compounds are useful intermediates in the above process.
PREPARATION OF BICYCLO[2.2.2]OCTAN-2-ONE COMPOUNDS
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Paragraph 0259; 0261-0262, (2013/08/28)
The present invention relates to a new process for the preparation of 6-hydroxy-5-arylbicyclo[2.2.2]octan-2-one compounds of the formula (II); which may subsequently be further transformed to compounds of the formula (I): The present invention further relates to novel compounds as such, which compounds are useful intermediates in the above process.
Design and scale-up of a practical enantioselective route to 5-Phenylbicyclo[2.2.2]oct-5-en-2-one
Abele, Stefan,Inauen, Roman,Funel, Jacques-Alexis,Weller, Thomas
, p. 129 - 140 (2012/06/01)
A practical enantioselective route to chiral 5-phenylbicyclo[2.2.2]oct-5- en-2-one 1 has been designed and developed. The target compound has been obtained as colorless crystals in 22% yield from 2-cyclohexenone, with an enantiomeric ratio higher than 99.5:0.5 and notably high chemical purity (> 99%). Three intermediates out of nine chemical steps are isolated. It is noteworthy that this process is devoid of any chromatography or distillation although all but one intermediate are oils. Key to success was the optimization of an intramolecular aldol reaction of an in situ prepared ketone aldehyde leading to the solid intermediate (1R,4R,4S,6S)-6-hydroxybicyclo[2.2.2]octan-2- one 9a that is isolated in very high chemical and chiral purity. This is an example of an intramolecular crystallization-induced diastereomer transformation (CIDT). The dehydration of this secondary alcohol to 1 required an extensive screen of reaction conditions to secure an excellent purity, essential for crystallization of this low-melting compound. The final process is simple and concentrated as demonstrated by an expeditious synthesis of 1 kg of 1 in a 30-L reactor in 10 working days.
