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Stereoselective Synthesis of Previously Unattainable Enantio(diastereo)enriched Bridged Tetrahydro-2-benzazepines.
Published: 19 October 2010 by MDPI in The 14th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
Abstract: A new and flexible route for the asymmetric synthesis of a variety of alkylated bridged tetrahydro-2-benzazepines has been developed. The key steps are the highly diastereoselective Michael addition of metalated SAMP-hydrazones to α,β-unsaturated esters combined with cyclomethylenation/Mitsunobu coupling reactions to secure the formation of the seven-membered azaheterocycle and of the bridged unit respectively.
Keywords: SAMP-hydrazones, Michael addition, cyclization, Mitsunobu reaction