Enantioenriched axially chiral β-diketimines: Determination of the IAN-amine barrier to atropisomerization
Enantioenriched axially chiral β-diketimines: Determination of the IAN-amine barrier to atropisomerization
复制标题
对映体富集的轴向手性 β-二酮亚胺：IAN-胺阻转异构化屏障的测定
DOI：
10.3987/com-03-s(p)62
复制
发表时间：
2004
期刊：
影响因子：
0.6
通讯作者：
J. Johnston
中科院分区：
文献类型：
--
作者：
Sarah B. Cortright;Ryan A. Yoder;J. Johnston
合成了由异喹啉和2-氨基萘衍生的对映体富集（> 98%ee）的β-二酮亚胺（IAN-胺）。一系列R-IAN胺（R = NH2，NHMe，NMe2）的热消旋反应显示出阻转异构化的高势垒（~30kcal/mol）和对氨基萘氮上取代的相对不敏感性。分子力学计算准确地预测了所观察到的相对取代基效应。
Enantioenriched (>98% ee) β-diketimines derived from Isoquinoline and 2-Amino Naphthalene ('IAN-amines') were prepared. Thermal racemization of a series of R-IAN amines (R = NH 2 , NHMe, NMe 2 ) revealed a high barrier to atropisomerization (~30 kcal/mol) and its relative insensitivity to substitution at the aminonaphthalene nitrogen. Molecular mechanics calculations accurately predicted the observed relative substituent effects.