Design and synthesis of a bis(hydroxyphenyl)diamide bearing a pendant thiazolium unit; application to the catalytic asymmetric intramolecular Stetter reaction

Design and synthesis of a bis(hydroxyphenyl)diamide bearing a pendant thiazolium unit; application to the catalytic asymmetric intramolecular Stetter reaction
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DOI:
10.1016/j.tetasy.2014.09.010
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发表时间:
2014-10-31
影响因子:
--
通讯作者:
Shibasaki, Masakatsu
Shibasaki, Masakatsu
中科院分区:
其他
文献类型:
--
作者:
Bao, Youmei;Kumagai, Naoya;Shibasaki, Masakatsu

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双(羟基苯基)二酰胺结构构成作为一个特权配体,促进了一些催化不对称转化与稀土金属的组合。设计、合成了一种新的二酰胺类化合物,该化合物具有由噻唑鎓单元衍生的卡宾催化功能,并将其应用于催化不对称分子内Stetter反应。卡宾官能团和氢键相互作用之间的协同作用,建议得到对映体富集的色满衍生物。(C)2014爱思唯尔有限公司版权所有。
The bis(hydroxyphenyl)diamide architecture constitutes as a privileged ligand that promotes a number of catalytic asymmetric transformations in combination with rare-earth metals. A new diamide analog armed with a carbene catalytic function derived from a thiazolium unit was designed, synthesized, and applied to the catalytic asymmetric intramolecular Stetter reaction. Cooperative work between the carbene function and hydrogen bonding interactions was suggested to give the enantioenriched chroman derivatives. (C) 2014 Elsevier Ltd. All rights reserved.