Journal
TETRAHEDRON
Volume 66, Issue 23, Pages 4115-4124Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.03.113
Keywords
Cyclocarbamation; 1,3-Oxazinan-2-ones; 1,3-Aminoalcohols; Piperidine-2,4-diones
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Funding
- Research Foundation - Flanders (FWO Flanders)
- Ghent University (BOF)
- Mersin University [BAP-SBE AKB 2009-3 DR]
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Halocyclocarbamation of benzyl N-(1-phenyl-3-butenyl)carbamates afforded 6-functionalized 4-aryl-1,3-oxazinan-2-ones with moderate to excellent diastereoselectivity depending on the N-substituent. Importantly, in contrast to reported cyclocarbamations of homoallylic carbamates, which are generally trans-diastereoselective, cyclization of N-unsubstituted Cbz-protected homoallylamines led to cis-1,3-oxazinan-2-ones, predominantly. The use of N-benzylated and in situ prepared N-silylated derivatives resulted however in trans-selectivity. Transition states are proposed to explain the stereochemical influence of the N-substituent on the cyclocarbamations. The functionalized 1,3-oxazinan-2-ones could be further elaborated towards biologically or synthetically important 6-arylpiperidine-2,4-diones and 3-aryl-1,3-aminoalcohols. (C) 2010 Elsevier Ltd. All rights reserved.
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