A study on the induction of stereoselectivity in the Strecker synthesis of basic amino acid-derived α-amino nitriles

被引：4
|
作者：
Ventosa-Andres, Pilar [1 ]
Teresa Garcia-Lopez, M. [1 ]
Herranz, Rosario [1 ]
机构：
[1] CSIC, Inst Quim Med, E-28006 Madrid, Spain
来源：
TETRAHEDRON-ASYMMETRY | 2012年 / 23卷 / 15-16期
关键词：
MOLECULAR DIVERSITY; CCK-4; ANALOGS; SCAFFOLDS; KETIMINES; SYSTEM;
D O I：
10.1016/j.tetasy.2012.07.009
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Diverse basic amino acid-derived alpha-amino nitriles have been synthesized via a modified Strecker reaction, using TMSCN as the cyanide source. It has been found that this synthesis is a slow thermodynamically controlled reaction, where it was difficult to induce stereocontrol. Moderate selectivity was induced by thermodynamic control of the reaction in MeOH. The absolute configuration at the stereogenic center generated was assigned by chemical correlation with 2-oxopiperazine derivatives. (c) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1198 / 1205
页数：8
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