Asymmetric hetero-Diels-Alder reactions. Mechanism of the reaction of alkenyloxazolines with isocyanates

Elliott, Mark Christopher ORCID: https://orcid.org/0000-0003-0132-0818, Kruiswijk, Elbertus and Willock, David James ORCID: https://orcid.org/0000-0002-8893-1090 1998. Asymmetric hetero-Diels-Alder reactions. Mechanism of the reaction of alkenyloxazolines with isocyanates. Tetrahedron Letters 39 (48) , pp. 8911-8914. 10.1016/S0040-4039(98)01949-2

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Abstract

Diastereomerically pure oxazolo[3,2-c]pyrimidines can be readily prepared by the reaction of alkenyloxazolines with isocyanates. These compounds undergo epimerisation upon prolonged heating. The mechanism of this transformation has been investigated experimentally and computationally. Diastereomerically pure oxazolo[3,2-c]pyrimidines can be prepared by hetero-Diels-Alder reaction of alkenyloxazolines. The mechanism of the formation and isomerisation of these compounds is discussed.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry Cardiff Catalysis Institute (CCI)
Subjects:	Q Science > QD Chemistry
Uncontrolled Keywords:	Asymmetric synthesis; Diels-Alder reaction
Publisher:	Elsevier
ISSN:	0040-4039
Funders:	Cardiff University, The Royal Society, The Nuffield Foundation, Pfizer Central Research, EPSRC, ICI Katalco, OCF
Last Modified:	18 Oct 2022 12:34
URI:	https://orca.cardiff.ac.uk/id/eprint/10373

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