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Synthesis 1990; 1990(7): 599-603
DOI: 10.1055/s-1990-26955
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Chiral Dienophiles Derived from Malic Acid: Synthesis of (Z)-(2S)-(tert-Butyl)-5-(ethoxycarbonylmethylene)-1,3-dioxolan-4-one and Its Diels-Alder Reaction with Cyclopentadiene

Georg Kneer* , Jochen Mattay, Gerhard Raabe, Carl Krüger, Jürgen Lauterwein
  • *Organisch-Chemisches Institut der Westfälischen Wilhelms-Universität Münster, Orléansring 23, D-4400 Münster, Federal Republic of Germany
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Publikationsdatum:
17. September 2002 (online)

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The synthesis of title chiral olefin 12 is described. Its structure is determined by X-ray analysis. The Diels-Alder reaction of 12 with cyclopentadiene exclusively yields the exo products with a face selectivity up to 95%.