Journal
TETRAHEDRON LETTERS
Volume 52, Issue 32, Pages 4109-4111Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.05.119
Keywords
Aza-Diels-Alder; 1-Azadienes; alpha-Amino acids; Pyridines
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Funding
- Direccion General de Investigacion del Ministerio de Ciencia e Innovacion (MICINN, Madrid DGI) [CTQ2009-12156]
- Departamento de Educacion
- Universidades e Investigacion del Gobierno Vasco
- Universidad del Pais Vasco [GV, IT 422-10: UPV, GIU-09/57]
- Ministerio de Ciencia e Innovacion
- European Social Fund
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A diastereoselective inverse electron demand aza-Diels-Alder reaction of N-aryl-1-azadienes derived from alpha-amino acids is accomplished using enamine dienophiles. Activation with ytterbium triflate of these azadienes affords dimeric structures through aza-Diels-Alder reaction, where the alkene double bond of 1-azadienes also adopts the role of dienophile. An asymmetric synthesis of functionalised 1,4,5,6-tetrahydropyridine compounds derived from alpha-amino acids using an optically active enamine is reported. (C) 2011 Elsevier Ltd. All rights reserved.
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