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Synthesis 1991; 1991(2): 133-140
DOI: 10.1055/s-1991-26398
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Tandem-Michael-Addition von 1-Cyanenaminen an Cyclohexenone. Ein neuer Zugang zu Bicyclo[2.2.2]octanonen

Hubertus Ahlbrecht* , Manfred Dietz, Claudia Schön, Volker Baumann
  • *Fachbereich Chemie der Universität Gießen, Institut für organische Chemie der Justus-Liebig-Universität, Heinrich-Buff-Ring 58, D-6300 Gießen, Germany
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Publication Date:
27 September 2002 (online)

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Tandem-Michael Addition of 1-Cyanoenamines to Cyclohexenones A New Access to Bicyclo[2.2.2]octanones Bicyclo[2.2.2]octane-2,5-diones 5 are easily obtained via tandem Michael addition of 2-(N-methylanilino)acrylonitrile (2) with deprotonated cyclohexenones 1. The reaction is highly anti-stereoselective with respect to substituents on C-4 and C-5 of the cyclohexenone and is blocked by disubstitution on C-4. 6-Acylbicyclo[2.2.2]octan-2-ones 25 are obtained by tandem Michael addition of deprotonated 2-(N-methylanilino) but-2-enonitrile (18) with cyclohexenone and subsequent protonation or alkylation. Both reactions gave lower yields or even failed with cyclopentenone and cycloheptenone.