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Chiral Lewis acid-catalyzed asymmetric Baylis-Hillman reactions
Kung-Shuo Yang1, Wei-Der Lee, Jia-Fu Pan
1Department of Chemistry, National Taiwan Normal University, Taipei, Taiwan 116, ROC.
The Journal of Organic Chemistry
|February 1, 2003
Abstract:
An effective chiral Lewis acid-catalyzed asymmetric Baylis-Hillman reaction is described. Good to high enantioselectivities were obtained using 3 mol % chiral catalyst. Novel camphor-derived dimerized ligands were prepared from the condensation of (+)-ketopinic acid with the corresponding diamines and hydrazine under acidic conditions. When alpha-naphthyl acrylate was used as a Michael acceptor, the reaction is complete within 20 min with high stereoselectivity and in reasonable chemical yields.