Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 22, Pages 4887-4894Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201300452
Keywords
Synthetic methods; Nitrogen heterocycles; Domino reactions; Microwave chemistry; Chiral auxiliaries
Categories
Funding
- Hungarian Research Foundation (OTKA) [T81371]
- [TAMOP 4.2.2/B-10/1-2010-0012]
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A simple protocol was introduced to prepare several enantiomerically pure heterocycles by using (-)-(1R, 2R, 3S, 4S)-3-aminonorbornene-2-carboxylic acid as a chiral auxiliary. The protocol is based on a domino ring-closure reaction, in which the relative configuration of the new asymmetric center is controlled by the stereochemistry of the amino acid, followed by a microwave-induced retro-Diels-Alder reaction.
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