Journal
TETRAHEDRON LETTERS
Volume 54, Issue 16, Pages 2101-2104Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.02.031
Keywords
Visible light; Photoredox catalysis; Iminium ion; 1,3-Oxazine; N,O-Acetal
Categories
Funding
- Research Corporation for Science Advancement
- Hendrix College
- Hendrix College, Odyssey Program
- National Science Foundation [1040470]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1040470] Funding Source: National Science Foundation
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1,3-Amino alcohols were prepared to examine how structure affects the oxidation of tertiary amines in visible light photocatalysis. These substrates were cyclized to produce oxazines following the photooxidative formation of iminium ions using catalytic Ru(bpy)(3)Cl-2. Amino alcohol derivatives of tetrahydroisoquinoline, tetrahydroquinoline, pyrrolidine, and Delta(3)-piperidine all were found to be viable substrates. In the case of the unsaturated piperidines, cyclization is accompanied by addition of methanol across the alkene; most likely occurring via a conjugate addition to an intermediate alpha,beta-unsaturated iminium ion prior to oxazine formation. (c) 2013 Elsevier Ltd. All rights reserved.
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