Asymmetric hetero-Diels-Alder reactions of alkenyldihydrooxazoles. Synthesis of oxazolo[3,2-c]pyrimidines and related compounds

Elliott, Mark Christopher ORCID: https://orcid.org/0000-0003-0132-0818 and Kruiswijk, Elbertus 1999. Asymmetric hetero-Diels-Alder reactions of alkenyldihydrooxazoles. Synthesis of oxazolo[3,2-c]pyrimidines and related compounds. Journal of the Chemical Society, Perkin Transactions 1 1999 (21) , pp. 3157-3166. 10.1039/a905700e

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Abstract

Alkenyldihydrooxazoles undergo a highly diastereoselective formal aza-Diels–Alder reaction with aryl and arenesulfonyl isocyanates to give oxazolo[3,2-c]pyrimidines. Depending on the substitution pattern of the alkenyldihydrooxazole, these compounds may then undergo addition of a second equivalent of the isocyanate to give either tetrahydrooxazolo[3,2-c]pyrimidine-8-carboxamides or octahydroazeto[2,3-d ]oxazolo[3,2-c]pyrimidines. The second addition is sensitive to steric and electronic factors, and can be prevented in some cases.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	RSC Publishing
ISSN:	0300-922X
Last Modified:	21 Oct 2022 10:21
URI:	https://orca.cardiff.ac.uk/id/eprint/39949

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