122847-32-9Relevant academic research and scientific papers
1,4-Pentadien-3-ones, 31. 1-(1-Cyclohexenyl)-1-propen-2-ones: Synthesis, Properties, and Stereoselective Formation of 3-Aryl-4-(1-cyclohexenylcarbonyl)perhydro-1-naphthalenones by Sequential Michael Reaction
Richter, Friedrich,Otto, Hans-Hartwig
, p. 7 - 14 (2007/10/02)
On rearrangement, 1-ethynyl-1-cyclohexanol (1) yields 1-acetyl-1-cyclohexene (2).At -78 deg C in the presence of LDA, 2 reacts with aldehydes/ketones yielding the aldols 5/8, which are dehydrated to the title compounds 6 or 9.At room temp., a reaction between the lithium derivative of 2 and 6 ensues, yielding the bicyclic products 10.These can also be prepared independently from isolated 6 and 2 with LDA or butyllithium in high yields.The stereochemistry is elucidated by spectroscopic methods, and the minimum energy conformation of 10a is calculated.Thestereoselective formation of 10 is explained by a lithium-controlled sequential Michael reaction.
