Journal
JOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume 694, Issue 11, Pages 1747-1753Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2008.11.050
Keywords
Alkenyl boronic acid; Alkenyl trifluoroborate; Salicylaldehyde; Chromene (benzopyran); Tocopherol; Dihydroquinoline; Quinoline
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Funding
- University of Southern California
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The one-step reaction of salicylaldehydes with amines and alkenyl boronic acids or alkenyl trifluoroborates to form 2H-chromenes (2H-1-benzopyrans) has been investigated in more detail and new suitable conditions have been identified, including the use of tertiary amines and protic solvents including water. This process was applied to a concise synthesis of a tocopherol analog. The analogous condensation reaction between 2-sulfamidobenzaldehydes and alkenyl trifluoroborates provides an efficient synthesis of 1,2-dihydroquinoline derivatives. (C) 2008 Elsevier B.V. All rights reserved.
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