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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

✍ Scribed by Richter, Friedrich ;Otto, Hans-Hartwig

Book ID
102901299
Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
878 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

On rearrangement, 1‐ethynyl‐1‐cyclohexanol (1) yields 1‐acetyl‐1‐cyclohexene (2). At −78°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. The stereoselective formation of 10 is explained by a lithium‐controlled sequential Michael reaction.

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