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Synthesis of spirocyclic compounds by the intramolecular michael reaction

✍ Scribed by H. A. P. de Jongh; Hans Wynberg


Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
557 KB
Volume
82
Category
Article
ISSN
0165-0513

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✦ Synopsis


Abstract

The double Michael reaction between the acyclic cross‐conjugated dienones dibenzalacetone or divinyl ketone and cyclohexane‐1,3‐diones gives new, substituted spiro [5,5] undecane‐l,5,9‐triones. Some of these are reduced to the corresponding spirodiketone or monoketone.


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Acceptor-substituted cycloalkenones 1 undergo an iron(III)catalyzed vinylogous Michael reactiona sequence of enone-dienol tautomerism, [4+2]-cycloaddition, and retro-aldol reactionwith quinone derivatives 3. A variety of products is obtained ranging from meta-terphenyl precursors 5 to