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Synlett 1999; 1999(9): 1379-1382
DOI: 10.1055/s-1999-2853
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Asymmetric Hetero-Diels-Alder Reactions with Heterocumulenes

Mark C. Elliott* , Alexandra E. Monk, Elbertus Kruiswijk, David E. Hibbs, Robert L. Jenkins, David V. Jones
  • *Department of Chemistry, Cardiff University, PO Box 912, Cardiff CF10 3TB, UK; Fax + 44(0 12 22)87 40 30; E-mail: elliottmc@cardiff.ac.uk
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Publication Date:
31 December 1999 (online)

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Chiral 2-alkenyloxazolines and 2-alkenylthiazolines react with isocyanates and ketenes to give formal hetero-Diels-Alder adducts with complete diastereocontrol. In each case an electron-rich double bond in the adduct is prone to a second addition of the heterocumulene. In the case of the oxazoline adducts the second addition is faster than the first, while with thiazolines the second addition is slower so that a different heterocumulene can be incorporated.

Diels-Alder reactions - heterocycles - isocyanates - ketenes - piperidines