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Synthesis 2000; 2000(14): 2060-2068
DOI: 10.1055/s-2000-8720
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Efficient Homologation of Aldehydes to 2,4,6-Alkatrienals by means of an α-(1,3-Dioxenylallyl)boronate

Reinhard W. Hoffmann* , Frank Schäfer, Eckart Haeberlin, Thorsten Rohde, Karsten Körber
  • *Fachbereich Chemie der Philipps-Universität Marburg, Hans-Meerwein-Strasse, 35032 Marburg, Germany; Fax +49(0)64 21 28 89 17; E-mail: rwho@ps1515.chemie.uni-marburg.de
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Publication Date:
31 December 2000 (online)

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The α-dioxenyl-allylboronate 4 allows the direct conversion of aldehydes into the 7-hydroxy-2,4-dienals (6). The latter compounds can be dehydrated to 2,4,6-alkatrienals 7 by means of the Burgess reagent or methanesulfonyl anhydride/Hünig Base.

allylboration reaction - polyenals