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Diasteroselective cyclizations with enantiopure malonaldehyde monocycloacetals
Lanrong Bi1, Ming Zhao, Chao Wang
1College of Pharmaceutical Sciences, Peking University, Beijing 100083, People's Republic of China.
The Journal of Organic Chemistry
|January 5, 2002
Abstract:
The synthesis of a series of enantiopure malonaldehyde monocycloacetals is described. Treatment of 8b with L-tryptophan methyl ester, 5-methoxytryptamine, and tryptamine, respectively, in the Pictet-Spengler condensation gave the corresponding enantiomerically pure key precursors 1-3 and 17-21 in only two steps. Using a chiral amino-diol successfully realized the kinetic resolution of racemic carbolines 23 and 24.