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Synthesis 1989; 1989(11): 836-843
DOI: 10.1055/s-1989-27405
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Asymmetrische Diels-Alder-Reaktionen von chiralen Isoprenylethern mit reaktiven Dienophilen

Roland Thiem* , Klaus Rotscheidt, Eberhard Breitmaier
  • *Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Str. 1, D-5300 Bonn 1, Federal Republic of Germany
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Publication Date:
02 May 2002 (online)

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Asymmetric Diels-Alder Reactions of Chiral Isoprenyl Ethers with Reactive Dienophiles The chiral alcohols 2 react with 3-ethoxy-2-methylacrolein (1) to yield chiral 3-alkoxy-2-methylacroleins 3, which are transformed to the chiral isoprenyl ethers 5 by Wittig methylenation in good yields. 1,3-Dienes 5 undergo [4+2] cycloadditions with reactive dienophiles such as maleic anhydride (6) or 4-phenyl-4H-1,2,4-triazol-3,5-dione (PTAD, 8) to afford the chiral cycloadduct 7 and 9 in moderate to good yield and diastereomeric excess. The resolution of the racemic alcohol trans-2-mesitylcyclohexanol 2d is reported.