ISSN:
0170-2041
Schlagwort(e):
1,4-Pentadien-3-one
;
1-Propen-2-one, 1-(1-cyclohexenyl)-
;
Aldol reaction
;
Michael reaction, stereoselective, sequential
;
1-Naphthalenone, perhydro-
;
Chemistry
;
Organic Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
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.
Zusätzliches Material:
1 Ill.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/jlac.199019900102
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