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Synlett 1990; 1990(3): 145-147
DOI: 10.1055/s-1990-21014
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Asymmetric Induction in Inverse Diels-Alder Reactions of the Chiral c,d-Olefin (2S)-2-(tert-Butyl)-5-methylene-1,3-dioxolan-4-one1

Jochen Mattay* , Georg Kneer, Jürgen Mertes
  • *Organisch-chemisches Institut der Westfälischen Wilhelms-Universität Münster, Orléans-Ring 23, D-4400 Münster, Federal Republic of Germany
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Publication Date:
08 March 2002 (online)

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The chiral c,d-olefin (2S)-2-(tert-butyl)-5-methylene-1,3, dioxolan-4-one(1) is an effective dienophile in normal and inverse Diels-Alder reactions. In the thermal reaction of 1 with ethyl 4-oxo-2-butenoate (2) only two of the four possible diastereoisomers are formed. Accordingly the reaction of 1 with acrolein (7) yields only one of the two possible Diels-Alder adducts.