ISSN:
0170-2041
Keywords:
1,4-Pentadien-3-one
;
1-Propen-2-one, 1-(1-cyclohexenyl)-
;
Aldol reaction
;
Michael reaction, stereoselective, sequential
;
1-Naphthalenone, perhydro-
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199019900102
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