文献类型：期刊文献

英文题名：Syntheses of chiral 1,3-disubstituted tetrahydro-β-carbolines via CIAT process: highly stereoselective Pictet-Spengler reaction of D-tryptophan ester hydrochlorides with various aldehydes

作者：Xiao, Sen[1];Lu, Xia[1];Shi, Xiao-Xin[1];Sun, Yu[1];Liang, Li-Li[1];Yu, Xin-Hong[1];Dong, Jing[1]

机构：[1]E China Univ Sci & Technol, Sch Pharm, Dept Pharmaceut Engn, Shanghai 200237, Peoples R China

年份：2009

卷号：20

期号：4

起止页码：430

外文期刊名：TETRAHEDRON-ASYMMETRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000265562600007)】；

基金：We thank the Chinese National Science Foundation (No. A-20172015) and Shanghai Educational Development Foundation (The Dawn Program: No. 03SG27) for the financial Support of this work.

语种：英文

摘要：A highly stereoselective Pictet-Spengler reaction of D-tryptophan methyl ester hydrochloride 1-HCl with various aldehydes via a CIAT (crystallization-induced asymmetric transformation) process is described. It was revealed that the CIAT process should be performed in a mixed solvent of nitromethane and toluene, and a fine tuning of the ratio of nitromethane and toluene for each epimer Mixture of 2-HCl was necessary in order to get as high yields and stereoselectivities as possible. Enantiomerically pure cis (or trans) 1,3-disubstituted tetrahydro-beta-carbolines 2a-2v were obtained by recrystallization or flash chromatography after neutralization of the corresponding hydrochloride salts cis-2-HCl or trans-2-HCl. (c) 2009 Elsevier Ltd. All rights reserved.