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

Elliott, Mark Christopher 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: 04 Jun 2017 04:29
URI: http://orca.cf.ac.uk/id/eprint/39949

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