Diasteroselective cyclizations with enantiopure malonaldehyde monocycloacetals

L Bi, M Zhao, C Wang, S Peng…

Index: Bi, Lanrong; Zhao, Ming; Wang, Chao; Peng, Shiqi European Journal of Organic Chemistry, 2000 , # 14 p. 2669 - 2676

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Citation Number: 16

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.

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