Influence of reaction conditions on products of the Pictet-Spengler condensation

被引：10
作者：
Pulka, Karolina [1 ]
Misicka, Aleksandra [1 ,2 ]
机构：
[1] Univ Warsaw, Fac Chem, PL-02093 Warsaw, Poland
[2] Polish Acad Sci, Med Res Ctr, PL-02106 Warsaw, Poland
来源：
TETRAHEDRON | 2011年 / 67卷 / 10期
关键词：
Condensation reaction; Pictet-Spengler reaction; Tetrahydro-beta-carbolines; alpha-Amino aldehydes; Bipyrroloindoles; ALPHA-AMINO ALDEHYDES; TETRAHYDRO-BETA-CARBOLINES; DERIVATIVES; TRYPTOPHAN; MECHANISM;
D O I：
10.1016/j.tet.2011.01.018
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Pictet-Spengler reaction with N-protected alpha-amino aldehydes was found to be very sensitive to reaction conditions. The outcome of the reaction can be controlled mainly by choice of solvent. Tetrahydro-beta-carbolines were obtained in apolar solvents, while in polar media octahydro-bipyrroloindoles were the main compounds. Temperature, amount of acid and reaction time also influenced the final results of the PS reaction. Depending on conditions, products with opposite configuration of stereogenic centre, descended from amino aldehydes, were formed as byproducts. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1955 / 1959
页数：5
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