Asymmetric Hetero-Diels-Alder Reactions with Heterocumulenes

Elliott, Mark Christopher ORCID: https://orcid.org/0000-0003-0132-0818, 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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Abstract

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:	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
URI:	https://orca.cardiff.ac.uk/id/eprint/39962

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