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Synthesis 1998; 1998(1): 83-88
DOI: 10.1055/s-1998-1995
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Mild and Stereoconvergent Palladium-Catalyzed Carbonyl Alkenation Reaction of α,β-Unsaturated Aldehydes

Manfred Braun* , Stefan Mroß, Ido Schwarz
  • *Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, D-40225 Düsseldorf, Germany; Fax + 49(2 11)8 11 30 85; E-mail: braunm@uni-duesseldorf.de
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Publication Date:
31 December 2000 (online)

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The addition of preformed ketone and ester enolates to α,β-unsaturated aldehydes 1 followed by in situ protection leads to the carbonates 3, 7, 8, 11, and 13. They are converted into sensitive functionalized dienes 4, 9, 12, and 14 by a smooth palladium-catalyzed elimination. Both syn- and anti-carbonates 7 and 8 lead to E-dienes 9 in a stereoconvergent manner.

aldol addition - elimination - palladium catalysis - dienes