Enantioselective inclusion of chiral alkyl aryl sulfoxides in a supramolecular helical channel consisting of an enantiopure 1,2-amino alcohol and an achiral carboxylic acid
Enantioselective inclusion of chiral alkyl aryl sulfoxides in a supramolecular helical channel consisting of an enantiopure 1,2-amino alcohol and an achiral carboxylic acid
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DOI：
10.1016/j.tetasy.2007.11.041
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发表时间：
2008-02-19
影响因子：
--
通讯作者：
Saigo, Kazuhiko
中科院分区：
文献类型：
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作者：
Kobayashi, Yuka;Soetrisno;Saigo, Kazuhiko
在由（1 R，2S）-2-氨基-1，2-二苯基乙醇1和非手性羧酸对叔丁基苯甲酸2或2-蒽醌羧酸3组成的双组分主体中，通过不对称一维螺旋通道，实现了烷基芳基亚砜4的对映体选择性包合物的形成. X-射线晶体学分析表明，在与甲基对甲基苯基亚砜4 n [（1 R，2S）-1.3.4n（单）]的包合物单晶中的主体骨架（1 R，2S）-1.3与包括溶剂的单晶（1 R，2S）-1.3-EtOH（单）和（1 R，2S）-1-3-H2O·THF（单）的那些保持超分子螺旋阵列，而客体4 n分子是高度无序的。此外，通过形成包合物获得的（1 R，2S）-1-3- 4 n（包合物）的X射线粉末衍射图表明，（1 R，2S）-1，3和4 n的分子排列与（1 R，2S）-1.3.4n（单一）中出现的分子排列不同，通道扩大。通过假设骨架（1 R，2S）-1-3的动态运动以实现广泛适用的笼形物形成来一致地解释这些结果。(c)2007爱思唯尔有限公司保留所有权利。
The enantio selective clathrate formation of alkyl aryl sulfoxides 4 was achieved with dissymmetric one-dimensional helical channels created in two-component hosts consisting of (1R,2S)-2-amino-1,2-diphenylethanol 1 and an achiral carboxylic acid, p-tert-butylbenzoic acid 2, or 2-anthraquinonecarboxylic acid 3. X-ray crystallographic analyses showed that the host framework (1R,2S)-1.3 in the single crystal of a clathrate with methyl p-methylphenyl sulfoxide 4n [(1R,2S)-1.3.4n (single)] maintained a supramolecular helical array as those of the solvent-included single crystals (1R,2S)-1.3-EtOH(single) and (1R,2S)-1-3-H2O.THF(single), while the guest 4n molecules were highly disordered. Moreover, the X-ray powder diffraction pattern of (1R,2S)-1-3-4n(clathrate) obtained through the clathrate formation demonstrated that the molecular arrangements of (1R,2S)-1, 3, and 4n were not the same as those which appeared in (1R,2S)-1.3.4n(single); the channel was enlarged. These results are consistently explained by assuming the dynamic motion of the framework (1R,2S)-1-3 to achieve widely applicable clathrate formation. (c) 2007 Elsevier Ltd. All rights reserved.