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Formation of Optically Pure Cyclic Amines by Intramolecular Conjugate Displacement

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posted on 06.04.2012, 00:00 by Ping Cheng, Derrick L. J. Clive
Intramolecular conjugate displacement (ICD) has been applied to the Morita–Baylis–Hillman adducts formed from (5S)-5-(l-menthyloxy)-2­(5H)-furanone and aldehydes that carry a protected β- or γ-amino group. DIBAL-H reduction of the resulting ICD products releases optically pure six- or seven-membered cyclic amines having a stereogenic center α to nitrogen.