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Azide 1,3-dipolar cycloadditions to N-propynoyl and N-propenoyl (5R)-5-phenylmorpholin-2-one: diastereocontrolled aziridine formation

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Chen, M.D., Gan, Y. and Harwood, L.M. ORCID: https://orcid.org/0000-0002-8442-7380 (2008) Azide 1,3-dipolar cycloadditions to N-propynoyl and N-propenoyl (5R)-5-phenylmorpholin-2-one: diastereocontrolled aziridine formation. Synlett (14). pp. 2119-2121. ISSN 0936-5214

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To link to this item DOI: 10.1055/s-2008-1078595

Abstract/Summary

N-Propynoyl (5R)-5-phenylmorpholin-2-one undergoes nonregioselective cycloaddition with aromatic azides to furnish mixtures of the corresponding triazoles, whereas N-propenoyl (5R)-5-phenylmorpholin-2-one reacts to furnish the corresponding diastereoisomerically pure aziridines in moderate to good yields, presumably via the intermediate triazolines.

Item Type:Article
Refereed:Yes
Divisions:Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:11126
Uncontrolled Keywords:(5R)-5-phenylmorpholin-2-one, triazole, triazoline, aziridine , STABILIZED AZOMETHINE YLIDES, ARYL AZIDES, DERIVATIVES, ALKYLATION, ACIDS
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