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Asymmetric Hetero-Diels-Alder Reactions with Heterocumulenes

Elliott, Mark Christopher ORCID:, Monk, Alexandra E., Kruiswijk, Elbertus, Hibbs, David E., Jenkins, Robert Leyshon and Jones, David V. 1999. Asymmetric Hetero-Diels-Alder Reactions with Heterocumulenes. Synlett 1999 (9) , pp. 1379-1382. 10.1055/s-1999-2853

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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: Diels-Alder reactions - heterocycles - isocyanates - ketenes - piperidines
Publisher: Georg Thieme Verlag
ISSN: 0936-5214
Last Modified: 21 Oct 2022 10:21

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